diff --git a/.changeset/add_math_and_markdown.md b/.changeset/add_math_and_markdown.md new file mode 100644 index 000000000..df1886f28 --- /dev/null +++ b/.changeset/add_math_and_markdown.md @@ -0,0 +1,15 @@ +--- +default: minor +--- + +# Markdown parser and render updates + +Migrated markdown parsing and rendering to use marked, which should fix most (all?) markdown issues involving lists/nested structures, inconsistent/inaccurate code blocks, escape sequences, and all the other bugs with literally everything. + +Added math rendering support via marked and KaTeX, uses standard `$$` and `$` delimiters. Only renders a subset of latex tags that will likely need to be expanded so feel free to make issues if needed. + +Also adds support for sending markdown tables (although they're rendered rather plainly at the moment), sending valid html directly (such as for colored text), and properly escaping anything with backslashes. + +Fixes link previews appearing in code blocks, fixes pmp new line behavior, fixes links not opening in new tabs, and fixes editing arbitrary html messages, probably. + +Finally, the old WYSIWYG editor has been completely removed. diff --git a/package.json b/package.json index 47bfe902f..69d23b0fc 100644 --- a/package.json +++ b/package.json @@ -70,8 +70,10 @@ "immer": "^9.0.21", "is-hotkey": "^0.2.0", "jotai": "^2.18.0", + "katex": "^0.16.45", "linkify-react": "^4.3.2", "linkifyjs": "^4.3.2", + "marked": "^18.0.2", "matrix-js-sdk": "^38.4.0", "matrix-widget-api": "^1.16.1", "pdfjs-dist": "^5.4.624", diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml index 02f7aba34..b5c82dbe2 100644 --- a/pnpm-lock.yaml +++ b/pnpm-lock.yaml @@ -135,12 +135,18 @@ importers: jotai: specifier: ^2.18.0 version: 2.18.1(@babel/core@7.29.0)(@babel/template@7.28.6)(@types/react@18.3.28)(react@18.3.1) + katex: + specifier: ^0.16.45 + version: 0.16.45 linkify-react: specifier: ^4.3.2 version: 4.3.2(linkifyjs@4.3.2)(react@18.3.1) linkifyjs: specifier: ^4.3.2 version: 4.3.2 + marked: + specifier: ^18.0.2 + version: 18.0.2 matrix-js-sdk: specifier: ^38.4.0 version: 38.4.0 @@ -3276,6 +3282,10 @@ packages: commander@2.20.3: resolution: {integrity: sha512-GpVkmM8vF2vQUkj2LvZmD35JxeJOLCwJ9cUkugyk2nuhbv3+mJvpLYYt+0+USMxE+oj+ey/lJEnhZw75x/OMcQ==} + commander@8.3.0: + resolution: {integrity: sha512-OkTL9umf+He2DZkUq8f8J9of7yL6RJKI24dVITBmNfZBmri9zYZQrKkuXiKhyfPSu8tUhnVBB1iKXevvnlR4Ww==} + engines: {node: '>= 12'} + common-tags@1.8.2: resolution: {integrity: sha512-gk/Z852D2Wtb//0I+kRFNKKE9dIIVirjoqPoA1wJU+XePVXZfGeBpk45+A1rKO4Q43prqWBNY/MiIeRLbPWUaA==} engines: {node: '>=4.0.0'} @@ -4039,6 +4049,10 @@ packages: resolution: {integrity: sha512-+KJGIyHgkGuIq3IEBNftfhW/LfWhXUIY6OmyVWjliu5KH1y0fw7VQ8YndE2O4qZdMSd9SqbnC8GOcZEy0Om7sA==} engines: {node: '>=18'} + katex@0.16.45: + resolution: {integrity: sha512-pQpZbdBu7wCTmQUh7ufPmLr0pFoObnGUoL/yhtwJDgmmQpbkg/0HSVti25Fu4rmd1oCR6NGWe9vqTWuWv3GcNA==} + hasBin: true + kleur@4.1.5: resolution: {integrity: sha512-o+NO+8WrRiQEE4/7nwRJhN1HWpVmJm511pBHUxPLtp0BUISzlBplORYSmTclCnJvQq2tKu/sgl3xVpkc7ZWuQQ==} engines: {node: '>=6'} @@ -4122,6 +4136,11 @@ packages: resolution: {integrity: sha512-hXdUTZYIVOt1Ex//jAQi+wTZZpUpwBj/0QsOzqegb3rGMMeJiSEu5xLHnYfBrRV4RH2+OCSOO95Is/7x1WJ4bw==} engines: {node: '>=10'} + marked@18.0.2: + resolution: {integrity: sha512-NsmlUYBS/Zg57rgDWMYdnre6OTj4e+qq/JS2ot3KrYLSoHLw+sDu0Nm1ZGpRgYAq6c+b1ekaY5NzVchMCQnzcg==} + engines: {node: '>= 20'} + hasBin: true + math-intrinsics@1.1.0: resolution: {integrity: sha512-/IXtbwEk5HTPyEwyKX6hGkYXxM9nbj64B+ilVJnC/R6B0pH5G4V3b0pVbL7DBj4tkhBAppbQUlf6F6Xl9LHu1g==} engines: {node: '>= 0.4'} @@ -8407,6 +8426,8 @@ snapshots: commander@2.20.3: {} + commander@8.3.0: {} + common-tags@1.8.2: {} compute-scroll-into-view@3.1.1: {} @@ -9224,6 +9245,10 @@ snapshots: jwt-decode@4.0.0: {} + katex@0.16.45: + dependencies: + commander: 8.3.0 + kleur@4.1.5: {} knip@5.85.0(@types/node@24.10.13)(typescript@5.9.3): @@ -9304,6 +9329,8 @@ snapshots: dependencies: semver: 7.7.4 + marked@18.0.2: {} + math-intrinsics@1.1.0: {} matrix-events-sdk@0.0.1: {} diff --git a/src/app/components/editor/Elements.tsx b/src/app/components/editor/Elements.tsx index 22487c03e..410d9aa98 100644 --- a/src/app/components/editor/Elements.tsx +++ b/src/app/components/editor/Elements.tsx @@ -1,4 +1,4 @@ -import { Scroll, Text } from 'folds'; +import { Text } from 'folds'; import type { RenderElementProps, RenderLeafProps } from 'slate-react'; import { useFocused, useSelected, useSlate } from 'slate-react'; import { useAtomValue } from 'jotai'; @@ -130,72 +130,6 @@ export function RenderElement({ attributes, element, children }: RenderElementPr {children} ); - case BlockType.Heading: - if (element.level === 1) - return ( - - {children} - - ); - if (element.level === 2) - return ( - - {children} - - ); - if (element.level === 3) - return ( - - {children} - - ); - return ( - - {children} - - ); - case BlockType.CodeLine: - return
{children}
; - case BlockType.CodeBlock: - return ( - - -
{children}
- - - ); - case BlockType.QuoteLine: - return
{children}
; - case BlockType.BlockQuote: - return ( - - {children} - - ); - case BlockType.ListItem: - return ( - - {children} - - ); - case BlockType.OrderedList: - return ( -
    - {children} -
- ); - case BlockType.UnorderedList: - return ( - - ); case BlockType.Mention: return ( @@ -220,19 +154,6 @@ export function RenderElement({ attributes, element, children }: RenderElementPr {children} ); - case BlockType.Small: - return ( - - {children} - - ); - case BlockType.HorizontalRule: - return ( -
-
- {children} -
- ); default: return ( - - {child} - - ); - if (leaf.italic) - child = ( - - - {child} - - ); - if (leaf.underline) - child = ( - - - {child} - - ); - if (leaf.strikeThrough) - child = ( - - - {child} - - ); - if (leaf.code) - child = ( - - - {child} - - ); - if (leaf.spoiler) - child = ( - - - {child} - - ); - - if (child !== children) return child; - - return {child}; +export function RenderLeaf({ attributes, children }: RenderLeafProps) { + return {children}; } diff --git a/src/app/components/editor/Toolbar.tsx b/src/app/components/editor/Toolbar.tsx deleted file mode 100644 index 4028b13c5..000000000 --- a/src/app/components/editor/Toolbar.tsx +++ /dev/null @@ -1,366 +0,0 @@ -import FocusTrap from 'focus-trap-react'; -import type { IconSrc, RectCords } from 'folds'; -import { - Badge, - Box, - config, - Icon, - IconButton, - Icons, - Line, - Menu, - PopOut, - Scroll, - Text, - Tooltip, - TooltipProvider, - toRem, -} from 'folds'; -import type { MouseEventHandler, ReactNode } from 'react'; -import { useState } from 'react'; -import { ReactEditor, useSlate } from 'slate-react'; -import { isMacOS } from '$utils/user-agent'; -import { KeySymbol } from '$utils/key-symbol'; -import { useSetting } from '$state/hooks/settings'; -import { settingsAtom } from '$state/settings'; -import { stopPropagation } from '$utils/keyboard'; -import { floatingToolbar } from '$styles/overrides/Composer.css'; -import type { HeadingLevel } from './slate'; -import { BlockType, MarkType } from './types'; -import * as css from './Editor.css'; -import { - headingLevel, - isAnyMarkActive, - isBlockActive, - isMarkActive, - removeAllMark, - toggleBlock, - toggleMark, -} from './utils'; - -function BtnTooltip({ text, shortCode }: { text: string; shortCode?: string }) { - return ( - - - {text} - {shortCode && ( - - - {shortCode} - - - )} - - - ); -} - -type MarkButtonProps = { format: MarkType; icon: IconSrc; tooltip: ReactNode }; -export function MarkButton({ format, icon, tooltip }: MarkButtonProps) { - const editor = useSlate(); - const disableInline = isBlockActive(editor, BlockType.CodeBlock); - - if (disableInline) { - removeAllMark(editor); - } - - const handleClick = () => { - toggleMark(editor, format); - ReactEditor.focus(editor); - }; - - return ( - - {(triggerRef) => ( - - - - )} - - ); -} - -type BlockButtonProps = { - format: BlockType; - icon: IconSrc; - tooltip: ReactNode; -}; -export function BlockButton({ format, icon, tooltip }: BlockButtonProps) { - const editor = useSlate(); - - const handleClick = () => { - toggleBlock(editor, format, { level: 1 }); - ReactEditor.focus(editor); - }; - - return ( - - {(triggerRef) => ( - - - - )} - - ); -} - -export function HeadingBlockButton() { - const editor = useSlate(); - const level = headingLevel(editor); - const [anchor, setAnchor] = useState(); - const isActive = isBlockActive(editor, BlockType.Heading); - const modKey = isMacOS() ? KeySymbol.Command : 'Ctrl'; - - const handleMenuSelect = (selectedLevel: HeadingLevel) => { - setAnchor(undefined); - toggleBlock(editor, BlockType.Heading, { level: selectedLevel }); - ReactEditor.focus(editor); - }; - - const handleMenuOpen: MouseEventHandler = (evt) => { - if (isActive) { - toggleBlock(editor, BlockType.Heading); - return; - } - setAnchor(evt.currentTarget.getBoundingClientRect()); - }; - return ( - setAnchor(undefined), - clickOutsideDeactivates: true, - isKeyForward: (evt: KeyboardEvent) => - evt.key === 'ArrowDown' || evt.key === 'ArrowRight', - isKeyBackward: (evt: KeyboardEvent) => evt.key === 'ArrowUp' || evt.key === 'ArrowLeft', - escapeDeactivates: stopPropagation, - }} - > - - - } - delay={500} - > - {(triggerRef) => ( - handleMenuSelect(1)} - size="400" - radii="300" - > - - - )} - - } - delay={500} - > - {(triggerRef) => ( - handleMenuSelect(2)} - size="400" - radii="300" - > - - - )} - - } - delay={500} - > - {(triggerRef) => ( - handleMenuSelect(3)} - size="400" - radii="300" - > - - - )} - - - - - } - > - - - - - - ); -} - -type ExitFormattingProps = { tooltip: ReactNode }; -export function ExitFormatting({ tooltip }: ExitFormattingProps) { - const editor = useSlate(); - - const handleClick = () => { - if (isAnyMarkActive(editor)) { - removeAllMark(editor); - } else if (!isBlockActive(editor, BlockType.Paragraph)) { - toggleBlock(editor, BlockType.Paragraph); - } - ReactEditor.focus(editor); - }; - - return ( - - {(triggerRef) => ( - - {`Exit ${KeySymbol.Hyper}`} - - )} - - ); -} - -export function Toolbar() { - const editor = useSlate(); - const modKey = isMacOS() ? KeySymbol.Command : 'Ctrl'; - const disableInline = isBlockActive(editor, BlockType.CodeBlock); - - const canEscape = isBlockActive(editor, BlockType.Paragraph) - ? isAnyMarkActive(editor) - : ReactEditor.isFocused(editor); - const [isMarkdown, setIsMarkdown] = useSetting(settingsAtom, 'isMarkdown'); - - return ( - - - - <> - - } - /> - } - /> - } - /> - } - /> - } - /> - } - /> - - - - - } - /> - } - /> - } - /> - } - /> - - - {canEscape && ( - <> - - - - } - /> - - - )} - - } - delay={500} - > - {(triggerRef) => ( - setIsMarkdown(!isMarkdown)} - aria-pressed={isMarkdown} - size="300" - radii="300" - disabled={disableInline || !!isAnyMarkActive(editor)} - > - - - )} - - - - - - - ); -} diff --git a/src/app/components/editor/getLinks.test.ts b/src/app/components/editor/getLinks.test.ts new file mode 100644 index 000000000..7f830a557 --- /dev/null +++ b/src/app/components/editor/getLinks.test.ts @@ -0,0 +1,89 @@ +import { describe, expect, it } from 'vitest'; +import type { Descendant } from 'slate'; +import { getLinks, toPlainText } from './output'; +import type { ParagraphElement } from './slate'; +import { BlockType } from './types'; + +describe('getLinks', () => { + it('extracts URLs from text', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Check out https://example.com for more info' }], + }; + const links = getLinks([node]); + expect(links).toContain('https://example.com'); + }); + + it('excludes URLs in angle brackets (Matrix HTML spoiler)', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Check out for more info' }], + }; + const links = getLinks([node]); + expect(links).toEqual([]); + }); + + it('extracts markdown link URLs', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Check [my link](https://example.com) for more info' }], + }; + const links = getLinks([node]); + expect(links).toContain('https://example.com'); + }); + + it('excludes URLs inside markdown inline code spans', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Do not visit `https://example.com` please' }], + }; + const links = getLinks([node]); + expect(links).toEqual([]); + }); + + it('excludes URLs inside markdown code blocks spanning multiple paragraphs', () => { + const nodes: Descendant[] = [ + { type: BlockType.Paragraph, children: [{ text: '```' }] }, + { type: BlockType.Paragraph, children: [{ text: 'https://example.com' }] }, + { type: BlockType.Paragraph, children: [{ text: '```' }] }, + ]; + const links = getLinks(nodes); + expect(links).toEqual([]); + }); +}); + +describe('toPlainText spoiler handling', () => { + it('replaces ||spoilered text|| with [Spoiler]', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Hello ||spoilered|| world' }], + }; + const plain = toPlainText(node); + expect(plain).toContain('[Spoiler]'); + expect(plain).not.toContain('||spoilered||'); + }); + + it('replaces ||spoilered links|| with [Spoiler]', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [{ text: 'Hello ||https://example.com|| world' }], + }; + const plain = toPlainText(node); + expect(plain).toContain('[Spoiler]'); + expect(plain).not.toContain('||https://example.com||'); + }); + + it('extracts non-spoilered markdown link URLs alongside spoilered ones', () => { + const node: ParagraphElement = { + type: BlockType.Paragraph, + children: [ + { + text: 'Check [visible](https://visible.com) and ||https://hidden.com||', + }, + ], + }; + const links = getLinks([node]); + expect(links).toContain('https://visible.com'); + expect(links).not.toContain('https://hidden.com'); + }); +}); diff --git a/src/app/components/editor/index.ts b/src/app/components/editor/index.ts index aae0137d1..09905d5f2 100644 --- a/src/app/components/editor/index.ts +++ b/src/app/components/editor/index.ts @@ -4,6 +4,6 @@ export * from './Editor'; export * from './Elements'; export * from './keyboard'; export * from './output'; -export * from './Toolbar'; + export * from './input'; export * from './types'; diff --git a/src/app/components/editor/input.ts b/src/app/components/editor/input.ts index b2476e437..7222cfcae 100644 --- a/src/app/components/editor/input.ts +++ b/src/app/components/editor/input.ts @@ -1,501 +1,15 @@ import type { Descendant } from 'slate'; -import { Text } from 'slate'; -import parse from 'html-dom-parser'; -import type { ChildNode, Element } from 'domhandler'; -import { isText, isTag } from 'domhandler'; -import { sanitizeCustomHtml } from '$utils/sanitize'; -import { - parseMatrixToRoom, - parseMatrixToRoomEvent, - parseMatrixToUser, - testMatrixTo, -} from '$plugins/matrix-to'; -import { escapeMarkdownInlineSequences, escapeMarkdownBlockSequences } from '$plugins/markdown'; -import { BlockType, MarkType } from './types'; -import type { - BlockQuoteElement, - CodeBlockElement, - CodeLineElement, - EmoticonElement, - HeadingElement, - HeadingLevel, - HorizontalRuleElement, - InlineElement, - MentionElement, - OrderedListElement, - ParagraphElement, - SmallElement, - UnorderedListElement, -} from './slate'; -import { createEmoticonElement, createMentionElement } from './utils'; +import { BlockType } from './types'; +import type { ParagraphElement } from './slate'; -type ProcessTextCallback = (text: string) => string; - -const getText = (node: ChildNode): string => { - if (isText(node)) { - return node.data; - } - if (isTag(node)) { - return node.children.map((child) => getText(child)).join(''); - } - return ''; -}; - -const getInlineNodeMarkType = (node: Element): MarkType | undefined => { - if (node.name === 'b' || node.name === 'strong') { - return MarkType.Bold; - } - - if (node.name === 'i' || node.name === 'em') { - return MarkType.Italic; - } - - if (node.name === 'u') { - return MarkType.Underline; - } - - if (node.name === 's' || node.name === 'del') { - return MarkType.StrikeThrough; - } - - if (node.name === 'code') { - if (node.parent && 'name' in node.parent && node.parent.name === 'pre') { - return undefined; // Don't apply `Code` mark inside a 
 tag
-    }
-    return MarkType.Code;
-  }
-
-  if (node.name === 'span' && node.attribs['data-mx-spoiler'] !== undefined) {
-    return MarkType.Spoiler;
-  }
-
-  return undefined;
-};
-
-const getInlineMarkElement = (
-  markType: MarkType,
-  node: Element,
-  getChild: (child: ChildNode) => InlineElement[]
-): InlineElement[] => {
-  const children = node.children.flatMap(getChild);
-  const mdSequence = node.attribs['data-md'];
-  if (mdSequence !== undefined) {
-    children.unshift({ text: mdSequence });
-    children.push({ text: mdSequence });
-    return children;
-  }
-  return children.map((child) => {
-    if (Text.isText(child)) {
-      return { ...child, [markType]: true };
-    }
-    return child;
-  });
-};
-
-const getInlineNonMarkElement = (node: Element): MentionElement | EmoticonElement | undefined => {
-  if (node.name === 'img' && node.attribs['data-mx-emoticon'] !== undefined) {
-    const { src, alt } = node.attribs;
-    if (!src) return undefined;
-    return createEmoticonElement(src, alt || 'Unknown Emoji');
-  }
-  if (node.name === 'a') {
-    const encodedHref = node.attribs.href;
-    const href = encodedHref && decodeURIComponent(encodedHref);
-    if (!href) return undefined;
-    if (testMatrixTo(href)) {
-      const userMention = parseMatrixToUser(href);
-      if (userMention) {
-        return createMentionElement(userMention, getText(node) || userMention, false);
-      }
-      const roomMention = parseMatrixToRoom(href);
-      if (roomMention) {
-        return createMentionElement(
-          roomMention.roomIdOrAlias,
-          getText(node) || roomMention.roomIdOrAlias,
-          false,
-          undefined,
-          roomMention.viaServers
-        );
-      }
-      const eventMention = parseMatrixToRoomEvent(href);
-      if (eventMention) {
-        return createMentionElement(
-          eventMention.roomIdOrAlias,
-          getText(node) || eventMention.roomIdOrAlias,
-          false,
-          eventMention.eventId,
-          eventMention.viaServers
-        );
-      }
-    }
-  }
-  return undefined;
-};
-
-const getInlineElement = (node: ChildNode, processText: ProcessTextCallback): InlineElement[] => {
-  if (isText(node)) {
-    return [{ text: processText(node.data) }];
-  }
-
-  if (isTag(node)) {
-    const markType = getInlineNodeMarkType(node);
-    if (markType) {
-      return getInlineMarkElement(markType, node, (child) => {
-        if (markType === MarkType.Code) return [{ text: getText(child) }];
-        return getInlineElement(child, processText);
-      });
-    }
-
-    const inlineNode = getInlineNonMarkElement(node);
-    if (inlineNode) return [inlineNode];
-
-    if (node.name === 'a') {
-      const children = node.childNodes.flatMap((child) => getInlineElement(child, processText));
-      children.unshift({ text: '[' });
-      children.push({ text: `](${node.attribs.href})` });
-      return children;
-    }
-
-    return node.childNodes.flatMap((child) => getInlineElement(child, processText));
-  }
-
-  return [];
-};
-
-const parseBlockquoteNode = (
-  node: Element,
-  processText: ProcessTextCallback
-): BlockQuoteElement[] | ParagraphElement[] => {
-  const quoteLines: Array = [];
-  let lineHolder: InlineElement[] = [];
-
-  const appendLine = () => {
-    if (lineHolder.length === 0) return;
-
-    quoteLines.push(lineHolder);
-    lineHolder = [];
-  };
-
-  node.children.forEach((child) => {
-    if (isText(child)) {
-      lineHolder.push({ text: processText(child.data) });
-      return;
-    }
-    if (isTag(child)) {
-      if (child.name === 'br') {
-        lineHolder.push({ text: '' });
-        appendLine();
-        return;
-      }
-
-      if (child.name === 'p') {
-        appendLine();
-        quoteLines.push(child.children.flatMap((c) => getInlineElement(c, processText)));
-        return;
-      }
-
-      lineHolder.push(...getInlineElement(child, processText));
-    }
-  });
-  appendLine();
-
-  const mdSequence = node.attribs['data-md'];
-  if (mdSequence !== undefined) {
-    return quoteLines.map((lineChildren) => ({
-      type: BlockType.Paragraph,
-      children: [{ text: `${mdSequence} ` }, ...lineChildren],
-    }));
-  }
-
-  return [
-    {
-      type: BlockType.BlockQuote,
-      children: quoteLines.map((lineChildren) => ({
-        type: BlockType.QuoteLine,
-        children: lineChildren,
-      })),
-    },
-  ];
-};
-const parseCodeBlockNode = (node: Element): CodeBlockElement[] | ParagraphElement[] => {
-  const codeLines = getText(node).trim().split('\n');
-
-  const mdSequence = node.attribs['data-md'];
-  if (mdSequence !== undefined) {
-    const pLines = codeLines.map((text) => ({
-      type: BlockType.Paragraph,
-      children: [{ text }],
-    }));
-    const childCode = node.children[0]!;
-    const className =
-      isTag(childCode) && childCode.tagName === 'code' ? (childCode.attribs.class ?? '') : '';
-    const prefix = { text: `${mdSequence}${className.replace('language-', '')}` };
-    const suffix = { text: mdSequence };
-    return [
-      { type: BlockType.Paragraph, children: [prefix] },
-      ...pLines,
-      { type: BlockType.Paragraph, children: [suffix] },
-    ];
-  }
-
-  return [
-    {
-      type: BlockType.CodeBlock,
-      children: codeLines.map((text) => ({
-        type: BlockType.CodeLine,
-        children: [{ text }],
-      })),
-    },
-  ];
-};
-const parseListNode = (
-  node: Element,
-  processText: ProcessTextCallback
-): OrderedListElement[] | UnorderedListElement[] | ParagraphElement[] => {
-  const listLines: Array = [];
-  let lineHolder: InlineElement[] = [];
-
-  const appendLine = () => {
-    if (lineHolder.length === 0) return;
-
-    listLines.push(lineHolder);
-    lineHolder = [];
-  };
-
-  node.children.forEach((child) => {
-    if (isText(child)) {
-      lineHolder.push({ text: processText(child.data) });
-      return;
-    }
-    if (isTag(child)) {
-      if (child.name === 'br') {
-        lineHolder.push({ text: '' });
-        appendLine();
-        return;
-      }
-
-      if (child.name === 'li') {
-        appendLine();
-        listLines.push(child.children.flatMap((c) => getInlineElement(c, processText)));
-        return;
-      }
-
-      lineHolder.push(...getInlineElement(child, processText));
-    }
-  });
-  appendLine();
-
-  const mdSequence = node.attribs['data-md'];
-  if (mdSequence !== undefined) {
-    const prefix = mdSequence || '-';
-    const [starOrHyphen] = prefix.match(/^\*|-$/) ?? [];
-    return listLines.map((lineChildren) => ({
-      type: BlockType.Paragraph,
-      children: [
-        { text: `${starOrHyphen ? `${starOrHyphen} ` : `${prefix}. `} ` },
-        ...lineChildren,
-      ],
-    }));
-  }
-
-  if (node.name === 'ol') {
-    return [
-      {
-        type: BlockType.OrderedList,
-        children: listLines.map((lineChildren) => ({
-          type: BlockType.ListItem,
-          children: lineChildren,
-        })),
-      },
-    ];
-  }
-
-  return [
-    {
-      type: BlockType.UnorderedList,
-      children: listLines.map((lineChildren) => ({
-        type: BlockType.ListItem,
-        children: lineChildren,
-      })),
-    },
-  ];
-};
-const parseHeadingNode = (
-  node: Element,
-  processText: ProcessTextCallback
-): HeadingElement | ParagraphElement => {
-  const children = node.children.flatMap((child) => getInlineElement(child, processText));
-
-  const headingMatch = node.name.match(/^h([123456])$/);
-  const [, g1AsLevel] = headingMatch ?? ['h3', '3'];
-  const level = Number.parseInt(g1AsLevel!, 10);
-
-  const mdSequence = node.attribs['data-md'];
-  if (mdSequence !== undefined) {
-    return {
-      type: BlockType.Paragraph,
-      children: [{ text: `${mdSequence} ` }, ...children],
-    };
-  }
-
-  return {
-    type: BlockType.Heading,
-    level: Math.min(level, 3) as HeadingLevel,
-    children,
-  };
-};
-
-const parseSmallNode = (
-  node: Element,
-  processText: ProcessTextCallback
-): SmallElement | ParagraphElement => {
-  const children = node.children.flatMap((child) => getInlineElement(child, processText));
-  const mdSequence = node.attribs['data-md'];
-
-  if (mdSequence !== undefined) {
-    return {
-      type: BlockType.Paragraph,
-      children: [{ text: `${mdSequence} ` }, ...children],
-    };
-  }
-
-  return {
-    type: BlockType.Small,
-    children,
-  };
-};
-
-const parseHorizontalRuleNode = (node: Element): HorizontalRuleElement | ParagraphElement => {
-  const mdSequence = node.attribs['data-md'];
-
-  if (mdSequence !== undefined) {
-    return {
-      type: BlockType.Paragraph,
-      children: [{ text: mdSequence }],
-    };
-  }
-
-  return {
-    type: BlockType.HorizontalRule,
-    children: [{ text: '' }],
-  };
-};
-
-export const domToEditorInput = (
-  domNodes: ChildNode[],
-  processText: ProcessTextCallback,
-  processLineStartText: ProcessTextCallback
-): Descendant[] => {
-  const children: Descendant[] = [];
-
-  let lineHolder: InlineElement[] = [];
-
-  const appendLine = () => {
-    if (lineHolder.length === 0) return;
-
-    children.push({
-      type: BlockType.Paragraph,
-      children: lineHolder,
-    });
-    lineHolder = [];
-  };
-
-  domNodes.forEach((node) => {
-    if (isText(node)) {
-      if (lineHolder.length === 0) {
-        // we are inserting first part of line
-        // it may contain block markdown starting data
-        // that we may need to escape.
-        lineHolder.push({ text: processLineStartText(node.data) });
-        return;
-      }
-      lineHolder.push({ text: processText(node.data) });
-      return;
-    }
-    if (isTag(node)) {
-      if (node.name === 'br') {
-        lineHolder.push({ text: '' });
-        appendLine();
-        return;
-      }
-
-      if (node.name === 'sub') {
-        appendLine();
-        children.push(parseSmallNode(node, processText));
-        return;
-      }
-
-      if (node.name === 'hr') {
-        appendLine();
-        children.push(parseHorizontalRuleNode(node));
-        return;
-      }
-
-      if (node.name === 'p') {
-        appendLine();
-        children.push({
-          type: BlockType.Paragraph,
-          children: node.children.flatMap((child) => getInlineElement(child, processText)),
-        });
-        return;
-      }
-
-      if (node.name === 'blockquote') {
-        appendLine();
-        children.push(...parseBlockquoteNode(node, processText));
-        return;
-      }
-      if (node.name === 'pre') {
-        appendLine();
-        children.push(...parseCodeBlockNode(node));
-        return;
-      }
-      if (node.name === 'ol' || node.name === 'ul') {
-        appendLine();
-        children.push(...parseListNode(node, processText));
-        return;
-      }
-
-      if (node.name.match(/^h[123456]$/)) {
-        appendLine();
-        children.push(parseHeadingNode(node, processText));
-        return;
-      }
-
-      lineHolder.push(...getInlineElement(node, processText));
-    }
-  });
-  appendLine();
-
-  return children;
-};
-
-export const htmlToEditorInput = (unsafeHtml: string, markdown?: boolean): Descendant[] => {
-  const sanitizedHtml = sanitizeCustomHtml(unsafeHtml);
-
-  const processText = (partText: string) => {
-    if (!markdown) return partText;
-    return escapeMarkdownInlineSequences(partText);
-  };
-
-  const domNodes = parse(sanitizedHtml);
-  const editorNodes = domToEditorInput(domNodes, processText, (lineStartText: string) => {
-    if (!markdown) return lineStartText;
-    return escapeMarkdownBlockSequences(lineStartText, processText);
-  });
-  return editorNodes;
-};
-
-export const plainToEditorInput = (text: string, markdown?: boolean): Descendant[] => {
+export const plainToEditorInput = (text: string): Descendant[] => {
   const editorNodes: Descendant[] = text.split('\n').map((lineText) => {
     const paragraphNode: ParagraphElement = {
       type: BlockType.Paragraph,
       children: [
         {
-          text: markdown
-            ? escapeMarkdownBlockSequences(lineText, escapeMarkdownInlineSequences)
-            : lineText,
+          text: lineText,
         },
       ],
     };
diff --git a/src/app/components/editor/keyboard.ts b/src/app/components/editor/keyboard.ts
index b45e9f9ab..7d9b18d58 100644
--- a/src/app/components/editor/keyboard.ts
+++ b/src/app/components/editor/keyboard.ts
@@ -1,116 +1,87 @@
 import { isKeyHotkey } from 'is-hotkey';
 import type { KeyboardEvent } from 'react';
-import { Editor, Element as SlateElement, Range, Transforms } from 'slate';
-import { isAnyMarkActive, isBlockActive, removeAllMark, toggleBlock, toggleMark } from './utils';
-import { BlockType, MarkType } from './types';
+import { Editor, Range, Transforms } from 'slate';
 
-export const INLINE_HOTKEYS: Record = {
-  'mod+b': MarkType.Bold,
-  'mod+i': MarkType.Italic,
-  'mod+u': MarkType.Underline,
-  'mod+s': MarkType.StrikeThrough,
-  'mod+[': MarkType.Code,
-  'mod+h': MarkType.Spoiler,
+export const INLINE_HOTKEYS: Record = {
+  'mod+b': '**',
+  'mod+i': '*',
+  'mod+u': '__',
+  'mod+s': '~~',
+  'mod+[': '`',
+  'mod+h': '||',
 };
 const INLINE_KEYS = Object.keys(INLINE_HOTKEYS);
 
-export const BLOCK_HOTKEYS: Record = {
-  'mod+7': BlockType.OrderedList,
-  'mod+8': BlockType.UnorderedList,
-  "mod+'": BlockType.BlockQuote,
-  'mod+;': BlockType.CodeBlock,
+export const BLOCK_HOTKEYS: Record = {
+  'mod+7': '1. ',
+  'mod+8': '- ',
+  "mod+'": '> ',
+  'mod+;': '```\n',
 };
 const BLOCK_KEYS = Object.keys(BLOCK_HOTKEYS);
 const isHeading1 = isKeyHotkey('mod+1');
 const isHeading2 = isKeyHotkey('mod+2');
 const isHeading3 = isKeyHotkey('mod+3');
 
+const insertMarkdownInline = (editor: Editor, marker: string) => {
+  if (editor.selection && Range.isExpanded(editor.selection)) {
+    const text = Editor.string(editor, editor.selection);
+    Transforms.insertText(editor, `${marker}${text}${marker}`);
+  } else {
+    Transforms.insertText(editor, `${marker}${marker}`);
+    Transforms.move(editor, { distance: marker.length, reverse: true });
+  }
+};
+
+const insertMarkdownBlock = (editor: Editor, prefix: string) => {
+  if (editor.selection) {
+    const path = editor.selection.anchor.path;
+    const startPoint = Editor.start(editor, path);
+    Transforms.insertText(editor, prefix, { at: startPoint });
+  }
+};
+
 /**
  * @return boolean true if shortcut is toggled.
  */
 export const toggleKeyboardShortcut = (editor: Editor, event: KeyboardEvent): boolean => {
-  if (isKeyHotkey('backspace', event) && editor.selection && Range.isCollapsed(editor.selection)) {
-    const startPoint = Range.start(editor.selection);
-    if (startPoint.offset !== 0) return false;
-
-    const [parentNode, parentPath] = Editor.parent(editor, startPoint);
-    const parentLocation = { at: parentPath };
-    const [previousNode] = Editor.previous(editor, parentLocation) ?? [];
-    const [nextNode] = Editor.next(editor, parentLocation) ?? [];
-
-    if (Editor.isEditor(parentNode)) return false;
-
-    if (parentNode.type === BlockType.Heading) {
-      toggleBlock(editor, BlockType.Paragraph);
-      return true;
-    }
-    if (
-      parentNode.type === BlockType.CodeLine ||
-      parentNode.type === BlockType.QuoteLine ||
-      parentNode.type === BlockType.ListItem
-    ) {
-      // exit formatting only when line block
-      // is first of last of it's parent
-      if (!previousNode || !nextNode) {
-        toggleBlock(editor, BlockType.Paragraph);
-        return true;
-      }
-    }
-    // Unwrap paragraph children to put them
-    // in previous none paragraph element
-    if (SlateElement.isElement(previousNode) && previousNode.type !== BlockType.Paragraph) {
-      Transforms.unwrapNodes(editor, {
-        at: startPoint,
-      });
-    }
-    Editor.deleteBackward(editor);
-    return true;
-  }
-
-  if (isKeyHotkey('mod+e', event) || isKeyHotkey('escape', event)) {
-    if (isAnyMarkActive(editor)) {
-      removeAllMark(editor);
-      return true;
-    }
-
-    if (!isBlockActive(editor, BlockType.Paragraph)) {
-      toggleBlock(editor, BlockType.Paragraph);
-      return true;
-    }
+  if (isKeyHotkey('escape', event)) {
     return false;
   }
 
   const blockToggled = BLOCK_KEYS.find((hotkey) => {
     if (isKeyHotkey(hotkey, event)) {
       event.preventDefault();
-      toggleBlock(editor, BLOCK_HOTKEYS[hotkey]!);
+      insertMarkdownBlock(editor, BLOCK_HOTKEYS[hotkey]!);
       return true;
     }
     return false;
   });
   if (blockToggled) return true;
+
   if (isHeading1(event)) {
-    toggleBlock(editor, BlockType.Heading, { level: 1 });
+    event.preventDefault();
+    insertMarkdownBlock(editor, '# ');
     return true;
   }
   if (isHeading2(event)) {
-    toggleBlock(editor, BlockType.Heading, { level: 2 });
+    event.preventDefault();
+    insertMarkdownBlock(editor, '## ');
     return true;
   }
   if (isHeading3(event)) {
-    toggleBlock(editor, BlockType.Heading, { level: 3 });
+    event.preventDefault();
+    insertMarkdownBlock(editor, '### ');
     return true;
   }
 
-  const inlineToggled = isBlockActive(editor, BlockType.CodeBlock)
-    ? false
-    : INLINE_KEYS.find((hotkey) => {
-        if (isKeyHotkey(hotkey, event)) {
-          event.preventDefault();
-          toggleMark(editor, INLINE_HOTKEYS[hotkey]!);
-          return true;
-        }
-        return false;
-      });
+  const inlineToggled = INLINE_KEYS.find((hotkey) => {
+    if (isKeyHotkey(hotkey, event)) {
+      event.preventDefault();
+      insertMarkdownInline(editor, INLINE_HOTKEYS[hotkey]!);
+      return true;
+    }
+    return false;
+  });
   return !!inlineToggled;
 };
diff --git a/src/app/components/editor/output.ts b/src/app/components/editor/output.ts
index d3efcd8dd..e4b6d01d7 100644
--- a/src/app/components/editor/output.ts
+++ b/src/app/components/editor/output.ts
@@ -2,22 +2,14 @@ import type { Descendant, Editor } from 'slate';
 import { Text } from 'slate';
 import type { MatrixClient } from '$types/matrix-sdk';
 import { sanitizeText } from '$utils/sanitize';
-import {
-  parseBlockMD,
-  parseInlineMD,
-  unescapeMarkdownBlockSequences,
-  unescapeMarkdownInlineSequences,
-} from '$plugins/markdown';
-import { findAndReplace } from '$utils/findAndReplace';
+import { markdownToHtml, injectDataMd } from '$plugins/markdown';
 import { sanitizeForRegex } from '$utils/regex';
 import { isUserId } from '$utils/matrix';
 import type { CustomElement } from './slate';
 import { BlockType } from './types';
+import { getMarkdownCodeSpanRanges, isInsideMarkdownCodeSpan } from './utils';
 
 export type OutputOptions = {
-  allowTextFormatting?: boolean;
-  allowInlineMarkdown?: boolean;
-  allowBlockMarkdown?: boolean;
   /**
    * if true it will remove the nickname of the person from the message
    */
@@ -28,48 +20,12 @@ export type OutputOptions = {
   nickNameReplacement?: Map;
 };
 
-const textToCustomHtml = (node: Text, opts: OutputOptions): string => {
-  let string = sanitizeText(node.text);
-  if (opts.allowTextFormatting) {
-    if (node.bold) string = `${string}`;
-    if (node.italic) string = `${string}`;
-    if (node.underline) string = `${string}`;
-    if (node.strikeThrough) string = `${string}`;
-    if (node.code) string = `${string}`;
-    if (node.spoiler) string = `${string}`;
-  }
-
-  if (opts.allowInlineMarkdown && string === sanitizeText(node.text) && !node.code) {
-    string = parseInlineMD(string);
-  }
-
-  return string;
-};
+const textToCustomHtml = (node: Text): string => sanitizeText(node.text);
 
 const elementToCustomHtml = (node: CustomElement, children: string): string => {
   switch (node.type) {
     case BlockType.Paragraph:
       return `${children}
`;
-    case BlockType.Heading:
-      return `${children}`;
-    case BlockType.CodeLine:
-      return `${children}\n`;
-    case BlockType.CodeBlock:
-      return `
${children}
`;
-    case BlockType.QuoteLine:
-      return `${children}
`;
-    case BlockType.BlockQuote:
-      return `
${children}
`;
-    case BlockType.ListItem:
-      return `
  • ${children}
    • `;
-    case BlockType.OrderedList:
-      return `
      ${children}
    `;
-    case BlockType.UnorderedList:
-      return `
      ${children}
    `;
-    case BlockType.Small:
-      return `${children}`;
-    case BlockType.HorizontalRule:
-      return `
    `;
 
     case BlockType.Mention: {
       let fragment = node.id;
@@ -82,7 +38,7 @@ const elementToCustomHtml = (node: CustomElement, children: string): string => {
       }
 
       const matrixTo = `https://matrix.to/#/${fragment}`;
-      return `${sanitizeText(node.name)}`;
+      return `${sanitizeText(node.name)}`;
     }
     case BlockType.Emoticon:
       return node.key.startsWith('mxc://')
@@ -91,7 +47,7 @@ const elementToCustomHtml = (node: CustomElement, children: string): string => {
           )}" title="${sanitizeText(node.shortcode)}" height="32" />`
         : sanitizeText(node.key);
     case BlockType.Link:
-      return `${children}`;
+      return `${children}`;
     case BlockType.Command:
       return `/${sanitizeText(node.command)}`;
     default:
@@ -99,15 +55,6 @@ const elementToCustomHtml = (node: CustomElement, children: string): string => {
   }
 };
 
-const HTML_TAG_REG_G = /<([\w-]+)(?: [^>]*)?(?:(?:\/>)|(?:>.*?<\/\1>))/g;
-const ignoreHTMLParseInlineMD = (text: string): string =>
-  findAndReplace(
-    text,
-    HTML_TAG_REG_G,
-    (match) => match[0],
-    (txt) => parseInlineMD(txt)
-  ).join('');
-
 /**
  * convert slate internal representation to a custom HTML string that can be sent to the server
  * @param node slate node
@@ -120,14 +67,12 @@ export const toMatrixCustomHTML = (
 ): string => {
   let markdownLines = '';
   const parseNode = (n: Descendant, index: number, targetNodes: Descendant[]) => {
-    if (opts.allowBlockMarkdown && 'type' in n && n.type === BlockType.Paragraph) {
-      let line = toMatrixCustomHTML(n, {
-        ...opts,
-        allowInlineMarkdown: false,
-        allowBlockMarkdown: false,
-      })
-        .replace(/$/, '\n')
-        .replace(/^(\\*)>/, '$1>');
+    if ('type' in n && n.type === BlockType.Paragraph) {
+      let line = toMatrixCustomHTML(n, opts);
+
+      // Use \n for all paragraphs to prevent extra blank lines from
+      // accumulating on each edit cycle.
+      line = line.replace(/$/, '\n').replace(/^(\\*)>/, '$1>');
 
       // strip nicknames if needed
       if (opts.stripNickname && opts.nickNameReplacement) {
@@ -138,21 +83,19 @@ export const toMatrixCustomHTML = (
       }
       markdownLines += line;
       if (index === targetNodes.length - 1) {
-        return parseBlockMD(markdownLines, ignoreHTMLParseInlineMD);
+        const html = markdownToHtml(markdownLines);
+        return injectDataMd(html);
       }
       return '';
     }
 
-    const parsedMarkdown = parseBlockMD(markdownLines, ignoreHTMLParseInlineMD);
+    const parsedMarkdown = markdownToHtml(markdownLines);
     markdownLines = '';
-    const isCodeLine = 'type' in n && n.type === BlockType.CodeLine;
-    if (isCodeLine) return `${parsedMarkdown}${toMatrixCustomHTML(n, {})}`;
-
-    return `${parsedMarkdown}${toMatrixCustomHTML(n, { ...opts, allowBlockMarkdown: false })}`;
+    return `${parsedMarkdown}${toMatrixCustomHTML(n, opts)}`;
   };
   if (Array.isArray(node))
     return node.map((element, index, array) => parseNode(element, index, array)).join('');
-  if (Text.isText(node)) return textToCustomHtml(node, opts);
+  if (Text.isText(node)) return textToCustomHtml(node);
 
   const children = node.children
     .map((element, index, array) => parseNode(element, index, array))
@@ -164,22 +107,6 @@ const elementToPlainText = (node: CustomElement, children: string): string => {
   switch (node.type) {
     case BlockType.Paragraph:
       return `${children}\n`;
-    case BlockType.Heading:
-      return `${children}\n`;
-    case BlockType.CodeLine:
-      return `${children}\n`;
-    case BlockType.CodeBlock:
-      return `${children}\n`;
-    case BlockType.QuoteLine:
-      return `| ${children}\n`;
-    case BlockType.BlockQuote:
-      return `${children}\n`;
-    case BlockType.ListItem:
-      return `- ${children}\n`;
-    case BlockType.OrderedList:
-      return `${children}\n`;
-    case BlockType.UnorderedList:
-      return `${children}\n`;
     case BlockType.Mention:
       return node.id;
     case BlockType.Emoticon:
@@ -188,10 +115,6 @@ const elementToPlainText = (node: CustomElement, children: string): string => {
       return `[${children}](${node.href})`;
     case BlockType.Command:
       return `/${node.command}`;
-    case BlockType.Small:
-      return `-# ${children}\n`;
-    case BlockType.HorizontalRule:
-      return `\n---\n`;
     default:
       return children;
   }
@@ -201,7 +124,7 @@ const SPOILERINPUTREGEX = /\|\|.+?\|\|/g;
 const LINK_URL = `(https?:\\/\\/.[A-Za-z0-9-._~:/?#[\\]()@!$&'*+,;%=]+)`;
 export const LINKINPUTREGEX = new RegExp(`\\(?(${LINK_URL})\\)?`, 'g');
 const SPOILEREDLINKINPUTREGEX = new RegExp(`<(${LINK_URL})>`, 'g');
-const MASKEDSPOILEREDLINKINPUTREGEX = new RegExp(`\\[.+\\]\\(${LINK_URL}\\)`, 'g');
+const SPOILEREDLINKDIRECTREGEX = new RegExp(`\\|\\|(${LINK_URL})\\|\\|`, 'g');
 
 /**
  * convert slate internal representation to a plain text string that can be sent to the server
@@ -213,12 +136,11 @@ const MASKEDSPOILEREDLINKINPUTREGEX = new RegExp(`\\[.+\\]\\(${LINK_URL}\\)`, 'g
  */
 export const toPlainText = (
   node: Descendant | Descendant[],
-  isMarkdown: boolean,
   stripNickname = false,
   nickNameReplacement?: Map
 ): string => {
   if (Array.isArray(node))
-    return node.map((n) => toPlainText(n, isMarkdown, stripNickname, nickNameReplacement)).join('');
+    return node.map((n) => toPlainText(n, stripNickname, nickNameReplacement)).join('');
   if (Text.isText(node)) {
     let { text } = node;
 
@@ -230,19 +152,41 @@ export const toPlainText = (
         const replacement = nickNameReplacement.get(key) ?? '';
         text = text.replaceAll(key, replacement);
       });
-      return isMarkdown
-        ? unescapeMarkdownBlockSequences(text, unescapeMarkdownInlineSequences)
-        : text;
     }
-    return isMarkdown
-      ? unescapeMarkdownBlockSequences(text, unescapeMarkdownInlineSequences)
-      : text;
+    return text;
   }
 
-  const children = node.children.map((n) => toPlainText(n, isMarkdown)).join('');
+  const children = node.children
+    .map((n) => toPlainText(n, stripNickname, nickNameReplacement))
+    .join('');
   return elementToPlainText(node, children);
 };
 
+/**
+ * Convert slate internal representation to a raw plain text string without any replacements.
+ * This is used for link extraction to ensure we have the full context for markdown blocks.
+ */
+export const toRawText = (node: Descendant | Descendant[]): string => {
+  if (Array.isArray(node)) return node.map(toRawText).join('');
+  if (Text.isText(node)) return node.text;
+
+  const children = node.children.map(toRawText).join('');
+  switch (node.type) {
+    case BlockType.Paragraph:
+      return `${children}\n`;
+    case BlockType.Link:
+      return `[${children}](${node.href})`;
+    case BlockType.Emoticon:
+      return node.key.startsWith('mxc://') ? `:${node.shortcode}:` : node.key;
+    case BlockType.Mention:
+      return node.id;
+    case BlockType.Command:
+      return `/${node.command}`;
+    default:
+      return children;
+  }
+};
+
 /**
  * Check if customHtml is equals to plainText
  * by replacing `
    ` with `/n` in customHtml
@@ -258,9 +202,11 @@ export const customHtmlEqualsPlainText = (customHtml: string, plain: string): bo
 export const trimCustomHtml = (customHtml: string) => customHtml.replaceAll(/$/g, '').trim();
 
 export const trimCommand = (cmdName: string, str: string) => {
-  const cmdRegX = new RegExp(`^(\\s+)?(\\/${sanitizeForRegex(cmdName)})([^\\S\n]+)?`);
+  const escapedCmd = sanitizeForRegex(cmdName);
+  // Allow optional leading whitespace and/or 
     tag for HTML strings
+  const cmdRegX = new RegExp(`^(?:\\s+)?(?:
    )?(?:\\/${escapedCmd})(?:[^\\S\n]+)?`, 'i');
 
-  const match = new RegExp(cmdRegX).exec(str);
+  const match = cmdRegX.exec(str);
   if (!match) return str;
   return str.slice(match[0].length);
 };
@@ -294,7 +240,6 @@ export const getMentions = (mx: MatrixClient, roomId: string, editor: Editor): M
 
   const parseMentions = (node: Descendant): void => {
     if (Text.isText(node)) return;
-    if (node.type === BlockType.CodeBlock) return;
 
     if (node.type === BlockType.Mention) {
       if (node.name === '@room') {
@@ -317,56 +262,40 @@ export const getMentions = (mx: MatrixClient, roomId: string, editor: Editor): M
 };
 
 export const getLinks = (serialized: Descendant | Descendant[]): string[] | undefined => {
-  let finalList: string[] = [];
-  let isInsideCodeBlock = false;
-  const parseLinks = (node: Descendant): void => {
-    if (Text.isText(node)) {
-      let { text } = node;
-      if (text.startsWith('```') && !text.includes(' ')) {
-        isInsideCodeBlock = !isInsideCodeBlock;
-        return;
-      }
-      if (isInsideCodeBlock) return;
-      // get a list of all the urls and of the ones that are spoilered,
-      // truncate the spoilered ones of their <> and then remove the items that are present in both lists
-      const urlsMatch = text.match(LINKINPUTREGEX);
-      let urls = urlsMatch ? [...new Set(urlsMatch)] : undefined;
-      urls = urls?.map(
-        (url) =>
-          (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
-          (url.startsWith('(') && url.substring(1)) ||
-          (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
-          url
-      );
-      const spoileredUrlsMatch = text.match(SPOILEREDLINKINPUTREGEX);
-      let spoileredUrls = spoileredUrlsMatch ? [...new Set(spoileredUrlsMatch)] : undefined;
-      spoileredUrls = spoileredUrls?.map((spoileredUrl) => spoileredUrl.slice(1, -1));
-
-      const maskedSpoileredUrlsMatch = text.match(MASKEDSPOILEREDLINKINPUTREGEX);
-      let maskedSpoileredUrls = maskedSpoileredUrlsMatch
-        ? [...new Set(maskedSpoileredUrlsMatch)]
-        : undefined;
-      maskedSpoileredUrls = maskedSpoileredUrls?.map((maskedSpoileredUrl) =>
-        maskedSpoileredUrl?.substring(
-          maskedSpoileredUrl.indexOf('](') + 2,
-          maskedSpoileredUrl.lastIndexOf(')')
-        )
-      );
-      if (maskedSpoileredUrls)
-        spoileredUrls = spoileredUrls
-          ? [...spoileredUrls, ...maskedSpoileredUrls]
-          : maskedSpoileredUrls;
-
-      spoileredUrls = spoileredUrls?.filter(
-        (item, index) => spoileredUrls?.indexOf(item) === index
-      );
-      urls = urls?.filter((url) => !spoileredUrls?.includes(url));
-      finalList = finalList.concat(urls ?? []);
-      return;
+  const text = toRawText(serialized);
+  const finalList = new Set();
+
+  // 1. Find all potential URLs
+  const urlsMatch = text.matchAll(LINKINPUTREGEX);
+  const spoileredUrlsMatch = [...text.matchAll(SPOILEREDLINKINPUTREGEX)].map((m) => m[1]);
+  const directSpoileredUrlsMatch = [...text.matchAll(SPOILEREDLINKDIRECTREGEX)].map((m) => m[1]);
+  const allSpoilered = new Set([...spoileredUrlsMatch, ...directSpoileredUrlsMatch]);
+
+  const codeSpanRanges = getMarkdownCodeSpanRanges(text);
+
+  for (const match of urlsMatch) {
+    let url = match[1]!;
+    const fullMatch = match[0];
+    const index = match.index;
+
+    // Clean up surrounding parens from markdown [label](url) or (url)
+    if (fullMatch.startsWith('(') && fullMatch.endsWith(')')) {
+      url = fullMatch.substring(1, fullMatch.length - 1);
+    } else if (fullMatch.startsWith('(')) {
+      url = fullMatch.substring(1);
+    } else if (fullMatch.endsWith('/)')) {
+      url = fullMatch.substring(0, fullMatch.length - 1);
     }
-    node?.children?.forEach(parseLinks);
-  };
-  if (Array.isArray(serialized)) serialized.map((n) => parseLinks(n));
-  else parseLinks(serialized);
-  return finalList.filter((item, index) => finalList.indexOf(item) === index);
+
+    if (allSpoilered.has(url)) continue;
+
+    // Check if it's inside a code span/block
+    if (isInsideMarkdownCodeSpan(index, index + fullMatch.length, codeSpanRanges)) {
+      continue;
+    }
+
+    finalList.add(url);
+  }
+
+  return Array.from(finalList);
 };
diff --git a/src/app/components/editor/slate.d.ts b/src/app/components/editor/slate.d.ts
index 05c8b5aec..7cca18623 100644
--- a/src/app/components/editor/slate.d.ts
+++ b/src/app/components/editor/slate.d.ts
@@ -3,22 +3,13 @@ import type { ReactEditor } from 'slate-react';
 import type { HistoryEditor } from 'slate-history';
 import type { BlockType } from './types';
 
-export type HeadingLevel = 1 | 2 | 3;
-
 export type Editor = BaseEditor & HistoryEditor & ReactEditor;
 
 export type Text = {
   text: string;
 };
 
-export type FormattedText = Text & {
-  bold?: boolean;
-  italic?: boolean;
-  underline?: boolean;
-  strikeThrough?: boolean;
-  code?: boolean;
-  spoiler?: boolean;
-};
+export type FormattedText = Text;
 
 export type LinkElement = {
   type: BlockType.Link;
@@ -47,77 +38,29 @@ export type CommandElement = {
   children: Text[];
 };
 
-export type InlineElement = Text | LinkElement | MentionElement | EmoticonElement | CommandElement;
+export type InlineElement =
+  | FormattedText
+  | LinkElement
+  | MentionElement
+  | EmoticonElement
+  | CommandElement;
 
 export type ParagraphElement = {
   type: BlockType.Paragraph;
   children: InlineElement[];
 };
-export type HeadingElement = {
-  type: BlockType.Heading;
-  level: HeadingLevel;
-  children: InlineElement[];
-};
-export type CodeLineElement = {
-  type: BlockType.CodeLine;
-  children: Text[];
-};
-export type CodeBlockElement = {
-  type: BlockType.CodeBlock;
-  children: CodeLineElement[];
-};
-export type QuoteLineElement = {
-  type: BlockType.QuoteLine;
-  children: InlineElement[];
-};
-export type BlockQuoteElement = {
-  type: BlockType.BlockQuote;
-  children: QuoteLineElement[];
-};
-export type ListItemElement = {
-  type: BlockType.ListItem;
-  children: InlineElement[];
-};
-export type OrderedListElement = {
-  type: BlockType.OrderedList;
-  children: ListItemElement[];
-};
-export type UnorderedListElement = {
-  type: BlockType.UnorderedList;
-  children: ListItemElement[];
-};
-
-export type SmallElement = {
-  type: BlockType.Small;
-  children: InlineElement[];
-};
-
-export type HorizontalRuleElement = {
-  type: BlockType.HorizontalRule;
-  children: Text[];
-};
 
 export type CustomElement =
   | LinkElement
   | MentionElement
   | EmoticonElement
   | CommandElement
-  | ParagraphElement
-  | HeadingElement
-  | CodeLineElement
-  | CodeBlockElement
-  | QuoteLineElement
-  | BlockQuoteElement
-  | ListItemElement
-  | OrderedListElement
-  | UnorderedListElement
-  | SmallElement
-  | HorizontalRuleElement;
+  | ParagraphElement;
 
 declare module 'slate' {
   interface CustomTypes {
     Editor: Editor;
     Element: CustomElement;
-    Text: FormattedText & Text;
+    Text: FormattedText;
   }
 }
diff --git a/src/app/components/editor/types.ts b/src/app/components/editor/types.ts
index 52115a3f4..a1cac110d 100644
--- a/src/app/components/editor/types.ts
+++ b/src/app/components/editor/types.ts
@@ -1,26 +1,7 @@
-export enum MarkType {
-  Bold = 'bold',
-  Italic = 'italic',
-  Underline = 'underline',
-  StrikeThrough = 'strikeThrough',
-  Code = 'code',
-  Spoiler = 'spoiler',
-}
-
 export enum BlockType {
   Paragraph = 'paragraph',
-  Heading = 'heading',
-  CodeLine = 'code-line',
-  CodeBlock = 'code-block',
-  QuoteLine = 'quote-line',
-  BlockQuote = 'block-quote',
-  ListItem = 'list-item',
-  OrderedList = 'ordered-list',
-  UnorderedList = 'unordered-list',
   Mention = 'mention',
   Emoticon = 'emoticon',
   Link = 'link',
   Command = 'command',
-  Small = 'sub',
-  HorizontalRule = 'hr',
 }
diff --git a/src/app/components/editor/utils.ts b/src/app/components/editor/utils.ts
index 254d7a5b7..03adabd90 100644
--- a/src/app/components/editor/utils.ts
+++ b/src/app/components/editor/utils.ts
@@ -1,154 +1,14 @@
 import type { BasePoint, BaseRange } from 'slate';
 import { Editor, Element, Point, Range, Text, Transforms } from 'slate';
-import { BlockType, MarkType } from './types';
+import { BlockType } from './types';
 import type {
   CommandElement,
   EmoticonElement,
   FormattedText,
-  HeadingLevel,
   LinkElement,
   MentionElement,
 } from './slate';
 
-const ALL_MARK_TYPE: MarkType[] = [
-  MarkType.Bold,
-  MarkType.Code,
-  MarkType.Italic,
-  MarkType.Spoiler,
-  MarkType.StrikeThrough,
-  MarkType.Underline,
-];
-
-export const isMarkActive = (editor: Editor, format: MarkType) => {
-  const marks = Editor.marks(editor);
-  return marks ? marks[format] === true : false;
-};
-
-export const isAnyMarkActive = (editor: Editor) => {
-  const marks = Editor.marks(editor);
-  return marks && !!ALL_MARK_TYPE.find((type) => marks[type] === true);
-};
-
-export const toggleMark = (editor: Editor, format: MarkType) => {
-  const isActive = isMarkActive(editor, format);
-
-  if (isActive) {
-    Editor.removeMark(editor, format);
-  } else {
-    Editor.addMark(editor, format, true);
-  }
-};
-
-export const removeAllMark = (editor: Editor) => {
-  ALL_MARK_TYPE.forEach((mark) => {
-    if (isMarkActive(editor, mark)) Editor.removeMark(editor, mark);
-  });
-};
-
-export const isBlockActive = (editor: Editor, format: BlockType) => {
-  const [match] = Editor.nodes(editor, {
-    match: (node) => Element.isElement(node) && node.type === format,
-  });
-
-  return !!match;
-};
-
-export const headingLevel = (editor: Editor): HeadingLevel | undefined => {
-  const [nodeEntry] = Editor.nodes(editor, {
-    match: (node) => Element.isElement(node) && node.type === BlockType.Heading,
-  });
-  const [node] = nodeEntry ?? [];
-  if (!node) return undefined;
-  if ('level' in node) return node.level;
-  return undefined;
-};
-
-type BlockOption = { level: HeadingLevel };
-const NESTED_BLOCK = new Set([
-  BlockType.OrderedList,
-  BlockType.UnorderedList,
-  BlockType.BlockQuote,
-  BlockType.CodeBlock,
-]);
-
-export const toggleBlock = (editor: Editor, format: BlockType, option?: BlockOption) => {
-  Transforms.collapse(editor, {
-    edge: 'end',
-  });
-  const isActive = isBlockActive(editor, format);
-
-  Transforms.unwrapNodes(editor, {
-    match: (node) => Element.isElement(node) && NESTED_BLOCK.has(node.type),
-    split: true,
-  });
-
-  if (isActive) {
-    Transforms.setNodes(editor, {
-      type: BlockType.Paragraph,
-    });
-    return;
-  }
-
-  if (format === BlockType.OrderedList || format === BlockType.UnorderedList) {
-    Transforms.setNodes(editor, {
-      type: BlockType.ListItem,
-    });
-    const block = {
-      type: format,
-      children: [],
-    };
-    Transforms.wrapNodes(editor, block);
-    return;
-  }
-  if (format === BlockType.CodeBlock) {
-    Transforms.setNodes(editor, {
-      type: BlockType.CodeLine,
-    });
-    const block = {
-      type: format,
-      children: [],
-    };
-    Transforms.wrapNodes(editor, block);
-    return;
-  }
-
-  if (format === BlockType.BlockQuote) {
-    Transforms.setNodes(editor, {
-      type: BlockType.QuoteLine,
-    });
-    const block = {
-      type: format,
-      children: [],
-    };
-    Transforms.wrapNodes(editor, block);
-    return;
-  }
-
-  if (format === BlockType.Heading) {
-    Transforms.setNodes(editor, {
-      type: format,
-      level: option?.level ?? 1,
-    });
-  }
-
-  if (format === BlockType.HorizontalRule) {
-    Transforms.insertNodes(editor, {
-      type: BlockType.HorizontalRule,
-      children: [{ text: '' }],
-    });
-    return;
-  }
-
-  if (format === BlockType.Small) {
-    Transforms.setNodes(editor, { type: BlockType.Small });
-    return;
-  }
-
-  Transforms.setNodes(editor, {
-    type: format,
-  });
-};
-
 export const resetEditor = (editor: Editor) => {
   Transforms.delete(editor, {
     at: {
@@ -157,8 +17,7 @@ export const resetEditor = (editor: Editor) => {
     },
   });
 
-  toggleBlock(editor, BlockType.Paragraph);
-  removeAllMark(editor);
+  Transforms.setNodes(editor, { type: BlockType.Paragraph });
 };
 
 export const resetEditorHistory = (editor: Editor) => {
@@ -286,3 +145,35 @@ export const getBeginCommand = (editor: Editor): string | undefined => {
     return secondInline.command;
   return undefined;
 };
+
+export const getMarkdownCodeSpanRanges = (text: string): [number, number][] => {
+  const ranges: [number, number][] = [];
+  let openRun: { start: number; length: number } | undefined;
+
+  for (let index = 0; index < text.length; index += 1) {
+    if (text[index] === '`') {
+      let runEnd = index;
+      while (runEnd < text.length && text[runEnd] === '`') {
+        runEnd += 1;
+      }
+
+      const runLength = runEnd - index;
+      if (!openRun) {
+        openRun = { start: index, length: runLength };
+      } else if (openRun.length === runLength) {
+        ranges.push([openRun.start, runEnd]);
+        openRun = undefined;
+      }
+
+      index = runEnd - 1;
+    }
+  }
+
+  return ranges;
+};
+
+export const isInsideMarkdownCodeSpan = (
+  start: number,
+  end: number,
+  codeSpanRanges: [number, number][]
+): boolean => codeSpanRanges.some(([rangeStart, rangeEnd]) => start > rangeStart && end < rangeEnd);
diff --git a/src/app/components/message/MsgTypeRenderers.tsx b/src/app/components/message/MsgTypeRenderers.tsx
index d94c92564..66430ac02 100644
--- a/src/app/components/message/MsgTypeRenderers.tsx
+++ b/src/app/components/message/MsgTypeRenderers.tsx
@@ -93,6 +93,57 @@ type MTextProps = {
   renderBundledPreviews?: (bundles: IPreviewUrlResponse[]) => ReactNode;
   style?: CSSProperties;
 };
+
+const getUrlsFromContent = (
+  content: Record,
+  renderUrlsPreview?: (urls: string[]) => ReactNode
+): { urls?: string[]; bundleContent?: BundleContent[] } => {
+  const body = typeof content.body === 'string' ? content.body : '';
+  const customBody =
+    typeof content.formatted_body === 'string' ? content.formatted_body : undefined;
+  const trimmedBody = trimReplyFromBody(body);
+
+  const urlsMatch = trimmedBody.match(LINKINPUTREGEX);
+  let urls = urlsMatch ? [...new Set(urlsMatch)] : undefined;
+  urls = urls?.map(
+    (url) =>
+      (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
+      (url.startsWith('(') && url.substring(1)) ||
+      (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
+      url
+  );
+
+  if (urls && customBody) {
+    // Filter out URLs that only appear inside  or 
     tags in the formatted body
+    const safeHtml = customBody
+      .replace(/]*>.*?<\/pre>/gs, '')
+      .replace(/]*>.*?<\/code>/gs, '');
+    const safeText = safeHtml.replace(/<[^>]*>/g, '');
+    const safeUrlsMatch = safeText.match(LINKINPUTREGEX);
+    let safeUrls = safeUrlsMatch ? [...new Set(safeUrlsMatch)] : [];
+    safeUrls = safeUrls.map(
+      (url) =>
+        (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
+        (url.startsWith('(') && url.substring(1)) ||
+        (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
+        url
+    );
+    const safeUrlsSet = new Set(safeUrls);
+    urls = urls.filter((url) => safeUrlsSet.has(url));
+  }
+
+  let bundleContent = content['com.beeper.linkpreviews'] as BundleContent[];
+  try {
+    bundleContent = bundleContent?.filter((bundle) => !!urls?.includes(bundle.matched_url));
+    if (renderUrlsPreview && bundleContent)
+      urls = bundleContent.map((bundle) => bundle.matched_url);
+  } catch {
+    urls = [];
+  }
+
+  return { urls, bundleContent };
+};
+
 export function MText({
   edited,
   content,
@@ -106,11 +157,15 @@ export function MText({
   const body = typeof content.body === 'string' ? content.body : '';
   const customBody =
     typeof content.formatted_body === 'string' ? content.formatted_body : undefined;
+  const cleanedMessage = useMemo(
+    () => customBody?.replace(/
  • (
    <\/p>)?<\/li>/gi, '

    • '),
+    [customBody]
+  );
 
   const trimmedBody = useMemo(() => trimReplyFromBody(body), [body]);
   const unwrappedForwardedContent = useMemo(
-    () => unwrapForwardedContent(customBody ?? body),
-    [customBody, body]
+    () => unwrapForwardedContent(cleanedMessage ?? customBody ?? body),
+    [cleanedMessage, customBody, body]
   );
 
   const isForwarded = useMemo(() => {
@@ -122,14 +177,15 @@ export function MText({
    * For the unwrapping of per-message profile fallbacks, we look for  tags with the data-mx-profile-fallback attribute
    */
   const unwrappedPerMessageProfileMessage = useMemo(
-    () => customBody?.replace(/]*data-mx-profile-fallback[^>]*>(.*?):\s*<\/strong>/i, ''),
-    [customBody]
+    () =>
+      cleanedMessage?.replace(/]*data-mx-profile-fallback[^>]*>(.*?):\s*<\/strong>/i, ''),
+    [cleanedMessage]
   );
 
   const isJumbo = useMemo(() => {
     if (!trimmedBody || trimmedBody.length >= 500) return false;
     if (
-      (unwrappedPerMessageProfileMessage ?? customBody)?.match(
+      (unwrappedPerMessageProfileMessage ?? cleanedMessage ?? customBody)?.match(
         /^(]*data-mx-emoticon[^>]*\/>){1,20}$/i
       )
     )
@@ -142,35 +198,17 @@ export function MText({
     }
 
     return true;
-  }, [unwrappedPerMessageProfileMessage, trimmedBody, customBody]);
+  }, [unwrappedPerMessageProfileMessage, cleanedMessage, trimmedBody, customBody]);
 
   if (!body && !customBody) return ;
 
-  let bundleContent: BundleContent[] | undefined;
-  const urlsMatch = trimmedBody.match(LINKINPUTREGEX);
-  let urls = urlsMatch ? [...new Set(urlsMatch)] : undefined;
-  urls = urls?.map(
-    (url) =>
-      (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
-      (url.startsWith('(') && url.substring(1)) ||
-      (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
-      url
-  );
-  bundleContent = content['com.beeper.linkpreviews'] as BundleContent[];
-  //small "fix" for if someone sends malformed objects (ie not arrays of objects)
-  try {
-    bundleContent = bundleContent?.filter((bundle) => !!urls?.includes(bundle.matched_url));
-    if (renderUrlsPreview && bundleContent)
-      urls = bundleContent.map((bundle) => bundle.matched_url);
-  } catch {
-    urls = [];
-  }
+  const { urls, bundleContent } = getUrlsFromContent(content, renderUrlsPreview);
 
   if ((content['com.beeper.per_message_profile'] as PerMessageProfileBeeperFormat)?.has_fallback) {
     // unwrap per-message profile fallback if present
     return (
       
@@ -203,13 +241,13 @@ export function MText({
   return (
     <>
       
         {renderBody({
           body: trimmedBody,
-          customBody: typeof customBody === 'string' ? customBody : undefined,
+          customBody: typeof cleanedMessage === 'string' ? cleanedMessage : undefined,
         })}
         {edited && }
       
@@ -239,6 +277,13 @@ export function MEmote({
   renderBundledPreviews,
 }: MEmoteProps) {
   const { body, formatted_body: customBody } = content;
+  const cleanedMessage = useMemo(
+    () =>
+      typeof customBody === 'string'
+        ? customBody.replace(/
  • (
    <\/p>)?<\/li>/gi, '

    • ')
+        : undefined,
+    [customBody]
+  );
   const [jumboEmojiSize] = useSetting(settingsAtom, 'jumboEmojiSize');
 
   if (typeof body !== 'string') {
@@ -247,37 +292,19 @@ export function MEmote({
   const trimmedBody = trimReplyFromBody(body);
   const isJumbo = JUMBO_EMOJI_REG.test(trimmedBody);
 
-  let bundleContent: BundleContent[] | undefined;
-  const urlsMatch = trimmedBody.match(LINKINPUTREGEX);
-  let urls = urlsMatch ? [...new Set(urlsMatch)] : undefined;
-  urls = urls?.map(
-    (url) =>
-      (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
-      (url.startsWith('(') && url.substring(1)) ||
-      (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
-      url
-  );
-  bundleContent = content['com.beeper.linkpreviews'] as BundleContent[];
-  //small "fix" for if someone sends malformed objects (ie not arrays of objects)
-  try {
-    bundleContent = bundleContent?.filter((bundle) => !!urls?.includes(bundle.matched_url));
-    if (renderUrlsPreview && bundleContent)
-      urls = bundleContent.map((bundle) => bundle.matched_url);
-  } catch {
-    urls = [];
-  }
+  const { urls, bundleContent } = getUrlsFromContent(content, renderUrlsPreview);
 
   return (
     <>
       
         {`${displayName} `}
         {renderBody({
           body: trimmedBody,
-          customBody: typeof customBody === 'string' ? customBody : undefined,
+          customBody: typeof cleanedMessage === 'string' ? cleanedMessage : undefined,
         })}
         {edited && }
       
@@ -305,6 +332,13 @@ export function MNotice({
   renderBundledPreviews,
 }: MNoticeProps) {
   const { body, formatted_body: customBody } = content;
+  const cleanedMessage = useMemo(
+    () =>
+      typeof customBody === 'string'
+        ? customBody.replace(/
  • (
    <\/p>)?<\/li>/gi, '

    • ')
+        : undefined,
+    [customBody]
+  );
   const [jumboEmojiSize] = useSetting(settingsAtom, 'jumboEmojiSize');
 
   if (typeof body !== 'string') {
@@ -313,36 +347,18 @@ export function MNotice({
   const trimmedBody = trimReplyFromBody(body);
   const isJumbo = JUMBO_EMOJI_REG.test(trimmedBody);
 
-  let bundleContent: BundleContent[] | undefined;
-  const urlsMatch = trimmedBody.match(LINKINPUTREGEX);
-  let urls = urlsMatch ? [...new Set(urlsMatch)] : undefined;
-  urls = urls?.map(
-    (url) =>
-      (url.startsWith('(') && url.endsWith(')') && url.substring(1, url.length - 1)) ||
-      (url.startsWith('(') && url.substring(1)) ||
-      (url.endsWith('/)') && url.substring(0, url.length - 1)) ||
-      url
-  );
-  bundleContent = content['com.beeper.linkpreviews'] as BundleContent[];
-  //small "fix" for if someone sends malformed objects (ie not arrays of objects)
-  try {
-    bundleContent = bundleContent?.filter((bundle) => !!urls?.includes(bundle.matched_url));
-    if (renderUrlsPreview && bundleContent)
-      urls = bundleContent.map((bundle) => bundle.matched_url);
-  } catch {
-    urls = [];
-  }
+  const { urls, bundleContent } = getUrlsFromContent(content, renderUrlsPreview);
 
   return (
     <>
       
         {renderBody({
           body: trimmedBody,
-          customBody: typeof customBody === 'string' ? customBody : undefined,
+          customBody: typeof cleanedMessage === 'string' ? cleanedMessage : undefined,
         })}
         {edited && }
       
diff --git a/src/app/components/upload-card/UploadDescriptionEditor.tsx b/src/app/components/upload-card/UploadDescriptionEditor.tsx
index 8c98a3050..8a4f72ff3 100644
--- a/src/app/components/upload-card/UploadDescriptionEditor.tsx
+++ b/src/app/components/upload-card/UploadDescriptionEditor.tsx
@@ -2,7 +2,7 @@ import type { KeyboardEventHandler } from 'react';
 import { useCallback, useEffect, useState, useRef } from 'react';
 import type { Room } from '$types/matrix-sdk';
 import type { RectCords } from 'folds';
-import { Box, Chip, Icon, IconButton, Icons, Line, PopOut, Spinner, Text, config } from 'folds';
+import { Box, Chip, Icon, IconButton, Icons, PopOut, Spinner, Text, config } from 'folds';
 import { Editor, Transforms } from 'slate';
 import { ReactEditor } from 'slate-react';
 import { isKeyHotkey } from 'is-hotkey';
@@ -11,11 +11,9 @@ import {
   AutocompletePrefix,
   CustomEditor,
   EmoticonAutocomplete,
-  Toolbar,
   createEmoticonElement,
   getAutocompleteQuery,
   getPrevWorldRange,
-  htmlToEditorInput,
   plainToEditorInput,
   moveCursor,
   toMatrixCustomHTML,
@@ -23,6 +21,7 @@ import {
   trimCustomHtml,
   useEditor,
 } from '$components/editor';
+import { htmlToMarkdown } from '$plugins/markdown';
 import { useSetting } from '$state/hooks/settings';
 import { settingsAtom } from '$state/settings';
 import { UseStateProvider } from '$components/UseStateProvider';
@@ -47,8 +46,6 @@ export function DescriptionEditor({
 }: Readonly) {
   const editor = useEditor();
   const [enterForNewline] = useSetting(settingsAtom, 'enterForNewline');
-  const [isMarkdown] = useSetting(settingsAtom, 'isMarkdown');
-  const [toolbar, setToolbar] = useState(false);
 
   const [autocompleteQuery, setAutocompleteQuery] =
     useState>();
@@ -56,18 +53,12 @@ export function DescriptionEditor({
   const prevValue = useRef(value);
   const initialized = useRef(false);
   const handleSave = useCallback(() => {
-    const plainText = toPlainText(editor.children, isMarkdown).trim();
+    const plainText = toPlainText(editor.children).trim();
 
-    const customHtml = trimCustomHtml(
-      toMatrixCustomHTML(editor.children, {
-        allowTextFormatting: true,
-        allowBlockMarkdown: isMarkdown,
-        allowInlineMarkdown: isMarkdown,
-      })
-    );
+    const customHtml = trimCustomHtml(toMatrixCustomHTML(editor.children, {}));
 
     onSave(plainText, customHtml || plainText);
-  }, [editor, isMarkdown, onSave]);
+  }, [editor, onSave]);
 
   useEffect(() => {
     const valueChanged = prevValue.current !== value;
@@ -88,17 +79,16 @@ export function DescriptionEditor({
       const safeValue = typeof normalizedValue === 'string' ? normalizedValue : '';
 
       const incomingPlainText = toPlainText(
-        htmlToEditorInput(safeValue, isMarkdown),
-        isMarkdown
+        plainToEditorInput(safeValue.includes('<') ? htmlToMarkdown(safeValue) : safeValue)
       ).trim();
-      const currentPlainText = toPlainText(editor.children, isMarkdown).trim();
+      const currentPlainText = toPlainText(editor.children).trim();
 
       if (currentPlainText === incomingPlainText && initialized.current) return;
 
       const isLikelyHtml = safeValue.includes('<') || safeValue.includes('>');
       const initialValue = isLikelyHtml
-        ? htmlToEditorInput(safeValue, isMarkdown)
-        : plainToEditorInput(safeValue, isMarkdown);
+        ? plainToEditorInput(htmlToMarkdown(safeValue))
+        : plainToEditorInput(safeValue);
 
       editor.children = initialValue;
       Editor.normalize(editor, { force: true });
@@ -106,7 +96,7 @@ export function DescriptionEditor({
 
       initialized.current = true;
     }
-  }, [value, editor, isMarkdown]);
+  }, [value, editor]);
 
   const handleKeyDown: KeyboardEventHandler = useCallback(
     (evt) => {
@@ -203,14 +193,6 @@ export function DescriptionEditor({
                   
                 
                 
-                   setToolbar(!toolbar)}
-                  >
-                    
-                  
                   
                     {(anchor: RectCords | undefined, setAnchor) => (
                       
                 
               
-              {toolbar && (
-                
-                  
-                  
-                
-              )}
             
           }
         />
diff --git a/src/app/features/room/RoomInput.tsx b/src/app/features/room/RoomInput.tsx
index db21b3544..3eb901dc6 100644
--- a/src/app/features/room/RoomInput.tsx
+++ b/src/app/features/room/RoomInput.tsx
@@ -22,7 +22,6 @@ import {
   Icon,
   IconButton,
   Icons,
-  Line,
   Menu,
   MenuItem,
   Overlay,
@@ -46,7 +45,6 @@ import {
   resetEditor,
   RoomMentionAutocomplete,
   toMatrixCustomHTML,
-  Toolbar,
   toPlainText,
   trimCustomHtml,
   UserMentionAutocomplete,
@@ -60,6 +58,7 @@ import {
   ANYWHERE_AUTOCOMPLETE_PREFIXES,
   BEGINNING_AUTOCOMPLETE_PREFIXES,
   getLinks,
+  BlockType,
 } from '$components/editor';
 import { EmojiBoard, EmojiBoardTab } from '$components/emoji-board';
 import { UseStateProvider } from '$components/UseStateProvider';
@@ -234,7 +233,7 @@ export const RoomInput = forwardRef(
     const mx = useMatrixClient();
     const useAuthentication = useMediaAuthentication();
     const [enterForNewline] = useSetting(settingsAtom, 'enterForNewline');
-    const [isMarkdown] = useSetting(settingsAtom, 'isMarkdown');
+
     const [hideActivity] = useSetting(settingsAtom, 'hideActivity');
     const [mentionInReplies] = useSetting(settingsAtom, 'mentionInReplies');
     const settingsLinkBaseUrl = useSettingsLinkBaseUrl();
@@ -285,7 +284,6 @@ export const RoomInput = forwardRef(
 
     const imagePackRooms: Room[] = useImagePackRooms(roomId, roomToParents);
 
-    const [toolbar, setToolbar] = useSetting(settingsAtom, 'editorToolbar');
     const [showAudioRecorder, setShowAudioRecorder] = useState(false);
     const audioRecorderRef = useRef(null);
     const micHoldStartRef = useRef(0);
@@ -506,7 +504,7 @@ export const RoomInput = forwardRef(
     };
 
     const handleSendUpload = async (uploads: UploadSuccess[]) => {
-      const plainText = toPlainText(editor.children, isMarkdown).trim();
+      const plainText = toPlainText(editor.children).trim();
 
       const contentsPromises = uploads.map(async (upload) => {
         const fileItem = selectedFiles.find((f) => f.file === upload.file);
@@ -719,8 +717,26 @@ export const RoomInput = forwardRef(
        * the plain text we will send
        */
       let serializedChildren = editor.children;
+      if (commandName) {
+        // Strip the empty text node and command node from the beginning of the first paragraph
+        const firstPara = serializedChildren[0];
+        if (
+          firstPara &&
+          'type' in firstPara &&
+          firstPara.type === BlockType.Paragraph &&
+          firstPara.children.length >= 2
+        ) {
+          serializedChildren = [
+            {
+              ...firstPara,
+              children: firstPara.children.slice(2),
+            },
+            ...serializedChildren.slice(1),
+          ];
+        }
+      }
       const outgoingTransformContext = {
-        isMarkdown,
+        isMarkdown: true,
         settingsLinkBaseUrl,
       };
 
@@ -729,16 +745,13 @@ export const RoomInput = forwardRef(
         serializedChildren = transform.apply(serializedChildren, outgoingTransformContext);
       });
 
-      let plainText = toPlainText(serializedChildren, isMarkdown, true, nicknameReplacement).trim();
+      let plainText = toPlainText(serializedChildren, true, nicknameReplacement).trim();
 
       /**
        * the html we will send
        */
       let customHtml = trimCustomHtml(
         toMatrixCustomHTML(serializedChildren, {
-          allowTextFormatting: true,
-          allowBlockMarkdown: isMarkdown,
-          allowInlineMarkdown: isMarkdown,
           stripNickname: true,
           nickNameReplacement: nicknameReplacement,
         })
@@ -852,7 +865,8 @@ export const RoomInput = forwardRef(
           } else {
             // we don't have a formatted body, but we need one
             content.format = 'org.matrix.custom.html';
-            content.formatted_body = `${htmlPrefix}${plainText}`;
+            const escapedBody = sanitizeText(plainText).replaceAll('\n', '
    ');
+            content.formatted_body = `${htmlPrefix}${escapedBody}`;
           }
         }
       }
@@ -966,7 +980,6 @@ export const RoomInput = forwardRef(
       replyEvent,
       mx,
       roomId,
-      isMarkdown,
       canSendReaction,
       pkCompatEnable,
       replyDraft,
@@ -1460,17 +1473,6 @@ export const RoomInput = forwardRef(
                 )}
               
 
-               setToolbar(!toolbar)}
-              >
-                
-              
               
                 {(emojiBoardTab: EmojiBoardTab | undefined, setEmojiBoardTab) => (
                   (
               
             
           }
-          bottom={
-            toolbar && (
-              
    
-                
-                
-              
    
-            )
-          }
         />
         {showSchedulePicker && (
           (
     const mx = useMatrixClient();
     const editor = useEditor();
     const [enterForNewline] = useSetting(settingsAtom, 'enterForNewline');
-    const [globalToolbar] = useSetting(settingsAtom, 'editorToolbar');
-    const [isMarkdown] = useSetting(settingsAtom, 'isMarkdown');
-    const [toolbar, setToolbar] = useState(globalToolbar);
     const isComposing = useComposingCheck();
 
     const [autocompleteQuery, setAutocompleteQuery] =
@@ -168,14 +164,8 @@ export const MessageEditor = as<'div', MessageEditorProps>(
     const [saveState, save] = useAsyncCallback(
       useCallback(async () => {
         const oldContent = mEvent.getContent();
-        let plainText = toPlainText(editor.children, isMarkdown).trim();
-        let customHtml = trimCustomHtml(
-          toMatrixCustomHTML(editor.children, {
-            allowTextFormatting: true,
-            allowBlockMarkdown: isMarkdown,
-            allowInlineMarkdown: isMarkdown,
-          })
-        );
+        let plainText = toPlainText(editor.children).trim();
+        let customHtml = trimCustomHtml(toMatrixCustomHTML(editor.children, {}));
 
         const [prevBody, prevCustomHtml, prevMentions] = getPrevBodyAndFormattedBody();
 
@@ -256,7 +246,7 @@ export const MessageEditor = as<'div', MessageEditorProps>(
 
         const links = getLinks(editor.children);
 
-        if (!customHtmlEqualsPlainText(customHtml, plainText)) {
+        if (pmpDisplayname || !customHtmlEqualsPlainText(customHtml, plainText)) {
           newContent.format = 'org.matrix.custom.html';
           newContent.formatted_body = customHtml;
           contentBody.format = 'org.matrix.custom.html';
@@ -295,7 +285,7 @@ export const MessageEditor = as<'div', MessageEditorProps>(
         content['m.new_content']['com.beeper.linkpreviews'] = content['com.beeper.linkpreviews'];
 
         return mx.sendMessage(roomId, content as RoomMessageEventContent);
-      }, [mx, editor, roomId, mEvent, isMarkdown, getPrevBodyAndFormattedBody, room])
+      }, [mx, editor, roomId, mEvent, getPrevBodyAndFormattedBody, room])
     );
 
     const handleSave = useCallback(() => {
@@ -357,10 +347,9 @@ export const MessageEditor = as<'div', MessageEditorProps>(
     useEffect(() => {
       const [body, customHtml] = getPrevBodyAndFormattedBody();
 
-      const initialValue =
-        typeof customHtml === 'string'
-          ? htmlToEditorInput(customHtml, isMarkdown)
-          : plainToEditorInput(typeof body === 'string' ? body : '', isMarkdown);
+      const initialValue = plainToEditorInput(
+        customHtml ? htmlToMarkdown(customHtml) : typeof body === 'string' ? body : ''
+      );
 
       Transforms.select(editor, {
         anchor: Editor.start(editor, []),
@@ -369,7 +358,7 @@ export const MessageEditor = as<'div', MessageEditorProps>(
 
       editor.insertFragment(initialValue);
       if (!mobileOrTablet()) ReactEditor.focus(editor);
-    }, [editor, getPrevBodyAndFormattedBody, isMarkdown]);
+    }, [editor, getPrevBodyAndFormattedBody]);
 
     useEffect(() => {
       if (saveState.status === AsyncStatus.Success) {
@@ -504,14 +493,6 @@ export const MessageEditor = as<'div', MessageEditorProps>(
                       
                     
                     
-                       setToolbar(!toolbar)}
-                      >
-                        
-                      
                       
                         {(anchor: RectCords | undefined, setAnchor) => (
                           (
                       
                     
                   
-                  {toolbar && (
-                    
    
-                      
-                      
-                    
    
-                  )}
                 
               }
             />
diff --git a/src/app/features/room/outgoingMessageTransforms.ts b/src/app/features/room/outgoingMessageTransforms.ts
index 497c5f62d..a1b41f061 100644
--- a/src/app/features/room/outgoingMessageTransforms.ts
+++ b/src/app/features/room/outgoingMessageTransforms.ts
@@ -1,11 +1,7 @@
 import type { Descendant } from 'slate';
-import {
-  hasSettingsLinksToRewriteInDescendants,
-  rewriteSettingsLinksInDescendants,
-} from './settingsLinkMessage';
+import { hasSettingsLinksToRewrite, rewriteSettingsLinks } from './settingsLinkMessage';
 
 export type OutgoingMessageTransformContext = {
-  isMarkdown: boolean;
   settingsLinkBaseUrl: string;
 };
 
@@ -16,13 +12,8 @@ export type OutgoingMessageTransform = {
 
 export const outgoingMessageTransforms: OutgoingMessageTransform[] = [
   {
-    apply: (children, context) =>
-      rewriteSettingsLinksInDescendants(children, context.settingsLinkBaseUrl, context.isMarkdown),
+    apply: (children, context) => rewriteSettingsLinks(children, context.settingsLinkBaseUrl),
     shouldApply: (children, context) =>
-      hasSettingsLinksToRewriteInDescendants(
-        children,
-        context.settingsLinkBaseUrl,
-        context.isMarkdown
-      ),
+      hasSettingsLinksToRewrite(children, context.settingsLinkBaseUrl),
   },
 ];
diff --git a/src/app/features/room/settingsLinkMessage.test.ts b/src/app/features/room/settingsLinkMessage.test.ts
index 44f2b3157..ca96f717e 100644
--- a/src/app/features/room/settingsLinkMessage.test.ts
+++ b/src/app/features/room/settingsLinkMessage.test.ts
@@ -1,10 +1,7 @@
 import { describe, expect, it } from 'vitest';
 import { toMatrixCustomHTML, toPlainText, trimCustomHtml } from '$components/editor/output';
 import { BlockType } from '$components/editor/types';
-import {
-  hasSettingsLinksToRewriteInDescendants,
-  rewriteSettingsLinksInDescendants,
-} from './settingsLinkMessage';
+import { hasSettingsLinksToRewrite, rewriteSettingsLinks } from './settingsLinkMessage';
 
 const settingsUrl =
   'https://app.example/settings/account?focus=display-name&moe.sable.client.action=settings';
@@ -16,7 +13,7 @@ const invalidSettingsUrl =
 describe('settingsLinkMessage', () => {
   it('detects bare settings links that need outgoing rewriting', () => {
     expect(
-      hasSettingsLinksToRewriteInDescendants(
+      hasSettingsLinksToRewrite(
         [
           {
             type: BlockType.Paragraph,
@@ -29,7 +26,7 @@ describe('settingsLinkMessage', () => {
   });
 
   it('rewrites bare settings links into message-friendly labels before serialization', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
@@ -39,22 +36,16 @@ describe('settingsLinkMessage', () => {
       'https://app.example'
     );
 
-    expect(toPlainText(rewritten, false).trim()).toBe(
+    expect(toPlainText(rewritten).trim()).toBe(
       `[Settings > Account > Display Name](${settingsUrl})`
     );
-    expect(
-      trimCustomHtml(
-        toMatrixCustomHTML(rewritten, {
-          allowTextFormatting: true,
-          allowBlockMarkdown: false,
-          allowInlineMarkdown: false,
-        })
-      )
-    ).toBe(`Settings > Account > Display Name`);
+    expect(trimCustomHtml(toMatrixCustomHTML(rewritten, {}))).toContain(
+      `Settings > Account > Display Name`
+    );
   });
 
   it('rewrites same-base settings links with extra query params', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
@@ -64,13 +55,13 @@ describe('settingsLinkMessage', () => {
       'https://app.example'
     );
 
-    expect(toPlainText(rewritten, false).trim()).toBe(
+    expect(toPlainText(rewritten).trim()).toBe(
       `[Settings > Account > Display Name](${settingsUrlWithExtraParam})`
     );
   });
 
   it('does not rewrite settings links that are already in markdown link syntax', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
@@ -80,107 +71,69 @@ describe('settingsLinkMessage', () => {
       'https://app.example'
     );
 
-    expect(toPlainText(rewritten, true).trim()).toBe(`[Display Name](${settingsUrl})`);
-  });
-
-  it('does not rewrite settings links inside code blocks', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
-      [
-        {
-          type: BlockType.CodeBlock,
-          children: [
-            {
-              type: BlockType.CodeLine,
-              children: [{ text: settingsUrl }],
-            },
-          ],
-        },
-      ],
-      'https://app.example'
-    );
-
-    expect(toPlainText(rewritten, false).trim()).toBe(settingsUrl);
-    expect(
-      trimCustomHtml(
-        toMatrixCustomHTML(rewritten, {
-          allowTextFormatting: true,
-          allowBlockMarkdown: false,
-          allowInlineMarkdown: false,
-        })
-      )
-    ).not.toContain(' {
     expect(
-      hasSettingsLinksToRewriteInDescendants(
+      hasSettingsLinksToRewrite(
         [
           {
             type: BlockType.Paragraph,
             children: [{ text: `\`${settingsUrl}\`` }],
           },
         ],
-        'https://app.example',
-        true
+        'https://app.example'
       )
     ).toBe(false);
 
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
           children: [{ text: `\`${settingsUrl}\`` }],
         },
       ],
-      'https://app.example',
-      true
+      'https://app.example'
     );
 
-    expect(toPlainText(rewritten, true).trim()).toBe(`\`${settingsUrl}\``);
-    expect(
-      trimCustomHtml(
-        toMatrixCustomHTML(rewritten, {
-          allowTextFormatting: true,
-          allowBlockMarkdown: false,
-          allowInlineMarkdown: true,
-        })
-      )
-    ).not.toContain('Settings > Account > Display Name');
+    expect(toPlainText(rewritten).trim()).toBe(`\`${settingsUrl}\``);
+    expect(trimCustomHtml(toMatrixCustomHTML(rewritten, {}))).not.toContain(
+      'Settings > Account > Display Name'
+    );
   });
 
   it('does not rewrite settings links inside markdown autolinks', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
           children: [{ text: `<${settingsUrl}>` }],
         },
       ],
-      'https://app.example',
-      true
+      'https://app.example'
     );
 
-    expect(toPlainText(rewritten, true).trim()).toBe(settingsUrl);
+    expect(toPlainText(rewritten).trim()).toBe(settingsUrl);
   });
 
   it('does not rewrite settings links inside literal html text', () => {
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
           children: [{ text: `Settings` }],
         },
       ],
-      'https://app.example',
-      true
+      'https://app.example'
     );
 
-    expect(toPlainText(rewritten, true).trim()).toBe(`Settings`);
+    expect(toPlainText(rewritten).trim()).toBe(`Settings`);
   });
 
   it('does not rewrite settings links with unknown focus ids', () => {
     expect(
-      hasSettingsLinksToRewriteInDescendants(
+      hasSettingsLinksToRewrite(
         [
           {
             type: BlockType.Paragraph,
@@ -191,7 +144,7 @@ describe('settingsLinkMessage', () => {
       )
     ).toBe(false);
 
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
@@ -201,12 +154,12 @@ describe('settingsLinkMessage', () => {
       'https://app.example'
     );
 
-    expect(toPlainText(rewritten, false).trim()).toBe(invalidSettingsUrl);
+    expect(toPlainText(rewritten).trim()).toBe(invalidSettingsUrl);
   });
 
   it('rewrites plain same-base hash-router settings links when given the runtime app base', () => {
     const hashRouterSettingsUrl = 'https://app.example/#/app/settings/account?focus=display-name';
-    const rewritten = rewriteSettingsLinksInDescendants(
+    const rewritten = rewriteSettingsLinks(
       [
         {
           type: BlockType.Paragraph,
@@ -216,7 +169,7 @@ describe('settingsLinkMessage', () => {
       'https://app.example/#/app'
     );
 
-    expect(toPlainText(rewritten, false).trim()).toBe(
+    expect(toPlainText(rewritten).trim()).toBe(
       `[Settings > Account > Display Name](${hashRouterSettingsUrl})`
     );
   });
diff --git a/src/app/features/room/settingsLinkMessage.ts b/src/app/features/room/settingsLinkMessage.ts
index 90fa4e1d6..e3f25523e 100644
--- a/src/app/features/room/settingsLinkMessage.ts
+++ b/src/app/features/room/settingsLinkMessage.ts
@@ -1,20 +1,13 @@
 import { find as findLinks } from 'linkifyjs';
 import type { Descendant } from 'slate';
 import { Text } from 'slate';
-import type {
-  BlockQuoteElement,
-  FormattedText,
-  HeadingElement,
-  InlineElement,
-  ListItemElement,
-  OrderedListElement,
-  ParagraphElement,
-  QuoteLineElement,
-  SmallElement,
-  UnorderedListElement,
-} from '$components/editor/slate';
+import type { FormattedText, InlineElement, ParagraphElement } from '$components/editor/slate';
 import { BlockType } from '$components/editor/types';
-import { createLinkElement } from '$components/editor/utils';
+import {
+  createLinkElement,
+  getMarkdownCodeSpanRanges,
+  isInsideMarkdownCodeSpan,
+} from '$components/editor/utils';
 import { getSettingsLinkLabel, parseSettingsLink } from '$features/settings/settingsLink';
 
 type RewritableSettingsLinkMatch = {
@@ -27,38 +20,6 @@ type RewritableSettingsLinkMatch = {
 const isMarkdownSettingsLink = (text: string, start: number, end: number): boolean =>
   text.slice(0, start).endsWith('](') && text.slice(end).startsWith(')');
 
-const getMarkdownCodeSpanRanges = (text: string): [number, number][] => {
-  const ranges: [number, number][] = [];
-  let openRun: { start: number; length: number } | undefined;
-
-  for (let index = 0; index < text.length; index += 1) {
-    if (text[index] === '`') {
-      let runEnd = index;
-      while (runEnd < text.length && text[runEnd] === '`') {
-        runEnd += 1;
-      }
-
-      const runLength = runEnd - index;
-      if (!openRun) {
-        openRun = { start: index, length: runLength };
-      } else if (openRun.length === runLength) {
-        ranges.push([openRun.start, runEnd]);
-        openRun = undefined;
-      }
-
-      index = runEnd - 1;
-    }
-  }
-
-  return ranges;
-};
-
-const isInsideMarkdownCodeSpan = (
-  start: number,
-  end: number,
-  codeSpanRanges: [number, number][]
-): boolean => codeSpanRanges.some(([rangeStart, rangeEnd]) => start > rangeStart && end < rangeEnd);
-
 const isMarkdownAutolink = (text: string, start: number, end: number): boolean =>
   text[start - 1] === '<' && text[end] === '>';
 
@@ -76,32 +37,26 @@ const isProtectedMarkdownContext = (
   text: string,
   start: number,
   end: number,
-  isMarkdown: boolean,
   codeSpanRanges: [number, number][]
 ): boolean =>
   isMarkdownSettingsLink(text, start, end) ||
-  (isMarkdown &&
-    (isInsideMarkdownCodeSpan(start, end, codeSpanRanges) ||
-      isMarkdownAutolink(text, start, end) ||
-      isInsideHtmlTag(text, start)));
+  isInsideMarkdownCodeSpan(start, end, codeSpanRanges) ||
+  isMarkdownAutolink(text, start, end) ||
+  isInsideHtmlTag(text, start);
 
 const getRewritableSettingsLinkMatches = (
   text: string,
-  baseUrl: string,
-  isMarkdown: boolean
+  baseUrl: string
 ): RewritableSettingsLinkMatch[] => {
   const matches = findLinks(text, 'url');
   if (matches.length === 0) return [];
 
-  const codeSpanRanges = isMarkdown ? getMarkdownCodeSpanRanges(text) : [];
+  const codeSpanRanges = getMarkdownCodeSpanRanges(text);
   return matches.flatMap((match) => {
     const href = match.value;
     const settingsLink = parseSettingsLink(baseUrl, href);
 
-    if (
-      !settingsLink ||
-      isProtectedMarkdownContext(text, match.start, match.end, isMarkdown, codeSpanRanges)
-    ) {
+    if (!settingsLink || isProtectedMarkdownContext(text, match.start, match.end, codeSpanRanges)) {
       return [];
     }
 
@@ -118,13 +73,11 @@ const getRewritableSettingsLinkMatches = (
 
 const hasRewritableSettingsLinksInInlineChildren = (
   children: InlineElement[],
-  baseUrl: string,
-  isMarkdown: boolean
+  baseUrl: string
 ): boolean =>
   children.some(
     (child) =>
-      Text.isText(child) &&
-      getRewritableSettingsLinkMatches(child.text, baseUrl, isMarkdown).length > 0
+      Text.isText(child) && getRewritableSettingsLinkMatches(child.text, baseUrl).length > 0
   );
 
 const createTextSegment = (node: FormattedText, text: string): FormattedText => ({
@@ -132,12 +85,8 @@ const createTextSegment = (node: FormattedText, text: string): FormattedText =>
   text,
 });
 
-const rewriteInlineText = (
-  node: FormattedText,
-  baseUrl: string,
-  isMarkdown: boolean
-): InlineElement[] => {
-  const matches = getRewritableSettingsLinkMatches(node.text, baseUrl, isMarkdown);
+const rewriteInlineText = (node: FormattedText, baseUrl: string): InlineElement[] => {
+  const matches = getRewritableSettingsLinkMatches(node.text, baseUrl);
   if (matches.length === 0) return [node];
 
   const rewritten: InlineElement[] = [];
@@ -161,125 +110,40 @@ const rewriteInlineText = (
   return rewritten.filter((child) => !Text.isText(child) || child.text.length > 0);
 };
 
-const rewriteInlineChildren = (
-  children: InlineElement[],
-  baseUrl: string,
-  isMarkdown: boolean
-): InlineElement[] =>
-  children.flatMap((child) =>
-    Text.isText(child) ? rewriteInlineText(child, baseUrl, isMarkdown) : [child]
-  );
-
-const rewriteInlineContainer = <
-  T extends ParagraphElement | HeadingElement | QuoteLineElement | ListItemElement | SmallElement,
->(
-  node: T,
-  baseUrl: string,
-  isMarkdown: boolean
-): T => ({
-  ...node,
-  children: rewriteInlineChildren(node.children, baseUrl, isMarkdown),
-});
-
-const rewriteBlockQuote = (
-  node: BlockQuoteElement,
-  baseUrl: string,
-  isMarkdown: boolean
-): BlockQuoteElement => ({
-  ...node,
-  children: node.children.map((child) => rewriteInlineContainer(child, baseUrl, isMarkdown)),
-});
-
-const rewriteOrderedList = (
-  node: OrderedListElement,
-  baseUrl: string,
-  isMarkdown: boolean
-): OrderedListElement => ({
-  ...node,
-  children: node.children.map((child) => rewriteInlineContainer(child, baseUrl, isMarkdown)),
-});
+const rewriteInlineChildren = (children: InlineElement[], baseUrl: string): InlineElement[] =>
+  children.flatMap((child) => (Text.isText(child) ? rewriteInlineText(child, baseUrl) : [child]));
 
-const rewriteUnorderedList = (
-  node: UnorderedListElement,
-  baseUrl: string,
-  isMarkdown: boolean
-): UnorderedListElement => ({
+const rewriteInlineContainer = (node: ParagraphElement, baseUrl: string): ParagraphElement => ({
   ...node,
-  children: node.children.map((child) => rewriteInlineContainer(child, baseUrl, isMarkdown)),
+  children: rewriteInlineChildren(node.children, baseUrl),
 });
 
-const hasSettingsLinksToRewriteInNode = (
-  node: Descendant,
-  baseUrl: string,
-  isMarkdown: boolean
-): boolean => {
+const hasSettingsLinksToRewriteInNode = (node: Descendant, baseUrl: string): boolean => {
   if (Text.isText(node)) {
-    return getRewritableSettingsLinkMatches(node.text, baseUrl, isMarkdown).length > 0;
+    return getRewritableSettingsLinkMatches(node.text, baseUrl).length > 0;
   }
 
   switch (node.type) {
     case BlockType.Paragraph:
-    case BlockType.Heading:
-    case BlockType.QuoteLine:
-    case BlockType.ListItem:
-    case BlockType.Small:
-      return hasRewritableSettingsLinksInInlineChildren(node.children, baseUrl, isMarkdown);
-    case BlockType.BlockQuote:
-    case BlockType.OrderedList:
-    case BlockType.UnorderedList:
-      return node.children.some((child) =>
-        hasSettingsLinksToRewriteInNode(child, baseUrl, isMarkdown)
-      );
-    case BlockType.CodeBlock:
-    case BlockType.CodeLine:
-    case BlockType.HorizontalRule:
-    case BlockType.Link:
-    case BlockType.Mention:
-    case BlockType.Emoticon:
-    case BlockType.Command:
-      return false;
+      return hasRewritableSettingsLinksInInlineChildren(node.children, baseUrl);
     default:
       return false;
   }
 };
 
-const rewriteNode = (node: Descendant, baseUrl: string, isMarkdown: boolean): Descendant => {
+const rewriteNode = (node: Descendant, baseUrl: string): Descendant => {
   if (Text.isText(node)) return node;
 
   switch (node.type) {
     case BlockType.Paragraph:
-    case BlockType.Heading:
-    case BlockType.QuoteLine:
-    case BlockType.ListItem:
-    case BlockType.Small:
-      return rewriteInlineContainer(node, baseUrl, isMarkdown);
-    case BlockType.BlockQuote:
-      return rewriteBlockQuote(node, baseUrl, isMarkdown);
-    case BlockType.OrderedList:
-      return rewriteOrderedList(node, baseUrl, isMarkdown);
-    case BlockType.UnorderedList:
-      return rewriteUnorderedList(node, baseUrl, isMarkdown);
-    case BlockType.CodeBlock:
-    case BlockType.CodeLine:
-    case BlockType.HorizontalRule:
-    case BlockType.Link:
-    case BlockType.Mention:
-    case BlockType.Emoticon:
-    case BlockType.Command:
-      return node;
+      return rewriteInlineContainer(node, baseUrl);
     default:
       return node;
   }
 };
 
-export const rewriteSettingsLinksInDescendants = (
-  children: Descendant[],
-  baseUrl: string,
-  isMarkdown = false
-): Descendant[] => children.map((child) => rewriteNode(child, baseUrl, isMarkdown));
+export const hasSettingsLinksToRewrite = (nodes: Descendant[], baseUrl: string): boolean =>
+  nodes.some((node) => hasSettingsLinksToRewriteInNode(node, baseUrl));
 
-export const hasSettingsLinksToRewriteInDescendants = (
-  children: Descendant[],
-  baseUrl: string,
-  isMarkdown = false
-): boolean => children.some((child) => hasSettingsLinksToRewriteInNode(child, baseUrl, isMarkdown));
+export const rewriteSettingsLinks = (nodes: Descendant[], baseUrl: string): Descendant[] =>
+  nodes.map((node) => rewriteNode(node, baseUrl));
diff --git a/src/app/features/settings/account/BioEditor.tsx b/src/app/features/settings/account/BioEditor.tsx
index 05f8c2f76..7d58172fb 100644
--- a/src/app/features/settings/account/BioEditor.tsx
+++ b/src/app/features/settings/account/BioEditor.tsx
@@ -2,7 +2,7 @@ import type { KeyboardEventHandler } from 'react';
 import { useCallback, useEffect, useState, useRef } from 'react';
 import type { Room } from '$types/matrix-sdk';
 import type { RectCords } from 'folds';
-import { Box, Chip, Icon, IconButton, Icons, Line, PopOut, Spinner, Text, config } from 'folds';
+import { Box, Chip, Icon, IconButton, Icons, PopOut, Spinner, Text, config } from 'folds';
 import { Editor, Transforms } from 'slate';
 import { ReactEditor } from 'slate-react';
 import { isKeyHotkey } from 'is-hotkey';
@@ -11,11 +11,9 @@ import {
   AutocompletePrefix,
   CustomEditor,
   EmoticonAutocomplete,
-  Toolbar,
   createEmoticonElement,
   getAutocompleteQuery,
   getPrevWorldRange,
-  htmlToEditorInput,
   plainToEditorInput,
   moveCursor,
   toMatrixCustomHTML,
@@ -23,6 +21,7 @@ import {
   trimCustomHtml,
   useEditor,
 } from '$components/editor';
+import { htmlToMarkdown } from '$plugins/markdown';
 import { useSetting } from '$state/hooks/settings';
 import { settingsAtom } from '$state/settings';
 import { UseStateProvider } from '$components/UseStateProvider';
@@ -43,9 +42,6 @@ const BIO_LIMIT = 1024;
 export function BioEditor({ value, isSaving, imagePackRooms, onSave }: BioEditorProps) {
   const editor = useEditor();
   const [enterForNewline] = useSetting(settingsAtom, 'enterForNewline');
-  const [globalToolbar] = useSetting(settingsAtom, 'editorToolbar');
-  const [isMarkdown] = useSetting(settingsAtom, 'isMarkdown');
-  const [toolbar, setToolbar] = useState(globalToolbar);
 
   const [autocompleteQuery, setAutocompleteQuery] =
     useState>();
@@ -56,25 +52,19 @@ export function BioEditor({ value, isSaving, imagePackRooms, onSave }: BioEditor
   const initialized = useRef(false);
 
   const updateStats = useCallback(() => {
-    const plainText = toPlainText(editor.children, isMarkdown).trim();
+    const plainText = toPlainText(editor.children).trim();
     setCharCount(plainText.length);
-  }, [editor, isMarkdown]);
+  }, [editor]);
 
   const handleSave = useCallback(() => {
-    const plainText = toPlainText(editor.children, isMarkdown).trim();
+    const plainText = toPlainText(editor.children).trim();
     if (plainText.length > BIO_LIMIT) return;
 
-    const customHtml = trimCustomHtml(
-      toMatrixCustomHTML(editor.children, {
-        allowTextFormatting: true,
-        allowBlockMarkdown: isMarkdown,
-        allowInlineMarkdown: isMarkdown,
-      })
-    );
+    const customHtml = trimCustomHtml(toMatrixCustomHTML(editor.children, {}));
 
     onSave(customHtml || plainText, plainText);
     setHasChanged(false);
-  }, [editor, isMarkdown, onSave]);
+  }, [editor, onSave]);
 
   useEffect(() => {
     const valueChanged = prevValue.current !== value;
@@ -95,17 +85,16 @@ export function BioEditor({ value, isSaving, imagePackRooms, onSave }: BioEditor
       const safeValue = typeof normalizedValue === 'string' ? normalizedValue : '';
 
       const incomingPlainText = toPlainText(
-        htmlToEditorInput(safeValue, isMarkdown),
-        isMarkdown
+        plainToEditorInput(safeValue.includes('<') ? htmlToMarkdown(safeValue) : safeValue)
       ).trim();
-      const currentPlainText = toPlainText(editor.children, isMarkdown).trim();
+      const currentPlainText = toPlainText(editor.children).trim();
 
       if (currentPlainText === incomingPlainText && initialized.current) return;
 
       const isLikelyHtml = safeValue.includes('<') || safeValue.includes('>');
       const initialValue = isLikelyHtml
-        ? htmlToEditorInput(safeValue, isMarkdown)
-        : plainToEditorInput(safeValue, isMarkdown);
+        ? plainToEditorInput(htmlToMarkdown(safeValue))
+        : plainToEditorInput(safeValue);
 
       editor.children = initialValue;
       Editor.normalize(editor, { force: true });
@@ -115,7 +104,7 @@ export function BioEditor({ value, isSaving, imagePackRooms, onSave }: BioEditor
       setHasChanged(false);
       updateStats();
     }
-  }, [value, editor, isMarkdown, updateStats]);
+  }, [value, editor, updateStats]);
 
   const handleKeyDown: KeyboardEventHandler = useCallback(
     (evt) => {
@@ -211,14 +200,6 @@ export function BioEditor({ value, isSaving, imagePackRooms, onSave }: BioEditor
                   
                 
                 
-                   setToolbar(!toolbar)}
-                  >
-                    
-                  
                   
                     {(anchor: RectCords | undefined, setAnchor) => (
                       
                 
               
-              {toolbar && (
-                
-                  
-                  
-                
-              )}
             
           }
         />
diff --git a/src/app/features/settings/general/General.tsx b/src/app/features/settings/general/General.tsx
index 061953d14..16cc92772 100644
--- a/src/app/features/settings/general/General.tsx
+++ b/src/app/features/settings/general/General.tsx
@@ -415,7 +415,6 @@ function DateAndTime() {
 
 function Editor({ isMobile }: Readonly<{ isMobile: boolean }>) {
   const [enterForNewline, setEnterForNewline] = useSetting(settingsAtom, 'enterForNewline');
-  const [isMarkdown, setIsMarkdown] = useSetting(settingsAtom, 'isMarkdown');
   const [hideActivity, setHideActivity] = useSetting(settingsAtom, 'hideActivity');
   const [hideReads, setHideReads] = useSetting(settingsAtom, 'hideReads');
   const [sendPresence, setSendPresence] = useSetting(settingsAtom, 'sendPresence');
@@ -444,13 +443,6 @@ function Editor({ isMobile }: Readonly<{ isMobile: boolean }>) {
           }
         />
       
-      
-        }
-        />
-      
       
          {
   it('reads account data on mount and applies it to the atom', () => {
     const remoteContent = {
       v: SETTINGS_SYNC_VERSION,
-      settings: { isMarkdown: false },
+      settings: { twitterEmoji: false },
     };
     mockMx.getAccountData.mockReturnValueOnce({
       getContent: () => remoteContent,
     });
 
-    const store = makeStore({ settingsSyncEnabled: true, isMarkdown: true });
+    const store = makeStore({ settingsSyncEnabled: true, twitterEmoji: true });
     renderHook(() => useSettingsSyncEffect(), { wrapper: makeWrapper(store) });
 
-    expect(store.get(settingsAtom).isMarkdown).toBe(false);
+    expect(store.get(settingsAtom).twitterEmoji).toBe(false);
   });
 
   it('sets lastSynced after loading from account data on mount', () => {
-    const remoteContent = { v: SETTINGS_SYNC_VERSION, settings: { isMarkdown: false } };
+    const remoteContent = { v: SETTINGS_SYNC_VERSION, settings: { twitterEmoji: false } };
     mockMx.getAccountData.mockReturnValueOnce({ getContent: () => remoteContent });
 
     const store = makeStore({ settingsSyncEnabled: true });
@@ -230,7 +230,7 @@ describe('useSettingsSyncEffect — echo-token loop prevention', () => {
   });
 
   it('skips re-applying an event that echoes our own upload token', async () => {
-    const store = makeStore({ settingsSyncEnabled: true, isMarkdown: true });
+    const store = makeStore({ settingsSyncEnabled: true, twitterEmoji: true });
     renderHook(() => useSettingsSyncEffect(), { wrapper: makeWrapper(store) });
 
     // Trigger the upload.
@@ -247,15 +247,15 @@ describe('useSettingsSyncEffect — echo-token loop prevention', () => {
     const echoEvent = makeSableSettingsEvent({
       v: SETTINGS_SYNC_VERSION,
       synctoken: echoToken,
-      settings: { isMarkdown: false }, // different — must be ignored
+      settings: { twitterEmoji: false }, // different — must be ignored
     });
 
     act(() => {
       callbackHolder.current?.(echoEvent);
     });
 
-    // isMarkdown should stay true (echo was ignored).
-    expect(store.get(settingsAtom).isMarkdown).toBe(true);
+    // twitterEmoji should stay true (echo was ignored).
+    expect(store.get(settingsAtom).twitterEmoji).toBe(true);
   });
 
   it('marks sync status as idle and updates lastSynced when own echo arrives', async () => {
@@ -290,12 +290,12 @@ describe('useSettingsSyncEffect — echo-token loop prevention', () => {
   });
 
   it('applies an event from another device (different or absent echo token)', () => {
-    const store = makeStore({ settingsSyncEnabled: true, isMarkdown: true });
+    const store = makeStore({ settingsSyncEnabled: true, twitterEmoji: true });
     renderHook(() => useSettingsSyncEffect(), { wrapper: makeWrapper(store) });
 
     const remoteEvent = makeSableSettingsEvent({
       v: SETTINGS_SYNC_VERSION,
-      settings: { isMarkdown: false },
+      settings: { twitterEmoji: false },
       // No synctoken — definitely from another device.
     });
 
@@ -303,6 +303,6 @@ describe('useSettingsSyncEffect — echo-token loop prevention', () => {
       callbackHolder.current?.(remoteEvent);
     });
 
-    expect(store.get(settingsAtom).isMarkdown).toBe(false);
+    expect(store.get(settingsAtom).twitterEmoji).toBe(false);
   });
 });
diff --git a/src/app/pages/client/ClientNonUIFeatures.tsx b/src/app/pages/client/ClientNonUIFeatures.tsx
index 8282e5daf..b9dcf30c6 100644
--- a/src/app/pages/client/ClientNonUIFeatures.tsx
+++ b/src/app/pages/client/ClientNonUIFeatures.tsx
@@ -745,7 +745,6 @@ function SentryTagsFeature() {
     Sentry.setTag('message_layout', String(settings.messageLayout));
     Sentry.setTag('message_spacing', settings.messageSpacing);
     Sentry.setTag('twitter_emoji', String(settings.twitterEmoji));
-    Sentry.setTag('is_markdown', String(settings.isMarkdown));
     Sentry.setTag('page_zoom', String(settings.pageZoom));
     if (settings.themeId) Sentry.setTag('theme_id', settings.themeId);
     // Additional high-value tags for bug reproduction
diff --git a/src/app/plugins/markdown/bidirectional.test.ts b/src/app/plugins/markdown/bidirectional.test.ts
new file mode 100644
index 000000000..b7aa44d5b
--- /dev/null
+++ b/src/app/plugins/markdown/bidirectional.test.ts
@@ -0,0 +1,119 @@
+import { describe, expect, it } from 'vitest';
+import { markdownToHtml } from './markdownToHtml';
+import { htmlToMarkdown } from './htmlToMarkdown';
+import { injectDataMd } from './injectDataMd';
+
+describe('bidirectional round-trip', () => {
+  it('round-trips headings', () => {
+    const markdown = '## Hello World';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('## Hello World');
+  });
+
+  it('round-trips bold text', () => {
+    const markdown = '**bold text**';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('**bold text**');
+  });
+
+  it('round-trips italic text', () => {
+    const markdown = '*italic text*';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('*italic text*');
+  });
+
+  it('round-trips inline code', () => {
+    const markdown = '`inline code`';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('`inline code`');
+  });
+
+  it('round-trips code blocks', () => {
+    const markdown = '```rust\nfn main() {}\n```';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('```rust');
+    expect(result).toContain('fn main()');
+  });
+
+  it('round-trips blockquotes', () => {
+    const markdown = '> Quote text';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('> Quote text');
+  });
+
+  it('round-trips unordered lists', () => {
+    const markdown = '- Item 1\n- Item 2';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('- Item 1');
+    expect(result).toContain('- Item 2');
+  });
+
+  it('round-trips ordered lists', () => {
+    const markdown = '1. First\n2. Second';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    // Note: marked normalizes ordered lists to start at 1, but we increment for output
+    expect(result).toContain('1. First');
+    expect(result).toContain('2. Second');
+  });
+
+  it('round-trips spoiler syntax', () => {
+    const markdown = '||hidden message||';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('||hidden message||');
+  });
+
+  it('round-trips inline math', () => {
+    const markdown = '$E = mc^2$';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('$E = mc^2$');
+  });
+
+  it('round-trips block math', () => {
+    const markdown = '$$x + y$$';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain('$$x + y$$');
+  });
+
+  it('does NOT parse k. as a list', () => {
+    const markdown = 'k.Hello world';
+    const html = markdownToHtml(markdown);
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    // Should NOT contain any list markers
+    expect(result).not.toContain('
  • ');
+    expect(result).not.toContain('
      ');
+    expect(result).not.toContain('
        ');
+    expect(result).toContain('k.');
+  });
+
+  it('round-trips img[data-mx-emoticon] tags', () => {
+    const html = ':blobcat:';
+    const injected = injectDataMd(html);
+    const result = htmlToMarkdown(injected);
+    expect(result).toContain(' {
-  if (text === '') return text;
-  let result: string | undefined;
-
-  if (!result) result = runBlockRule(text, CodeBlockRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, HorizontalRuleRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, BlockQuoteRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, OrderedListRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, UnorderedListRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, SmallRule, parseBlockMD, parseInline);
-  if (!result) result = runBlockRule(text, HeadingRule, parseBlockMD, parseInline);
-
-  // replace \n with 
         because want to preserve empty lines
-  if (!result) {
-    result = text
-      .split('\n')
-      .map((lineText) => {
-        const match = lineText.match(ESC_BLOCK_SEQ);
-        if (!match) {
-          return parseInline?.(lineText) ?? lineText;
-        }
-
-        const [, g1] = match;
-        return replaceMatch(lineText, match, g1, (t) => [parseInline?.(t) ?? t]).join('');
-      })
-      .join('
        ');
-  }
-
-  return result ?? text;
-};
diff --git a/src/app/plugins/markdown/block/rules.ts b/src/app/plugins/markdown/block/rules.ts
deleted file mode 100644
index 370527a3d..000000000
--- a/src/app/plugins/markdown/block/rules.ts
+++ /dev/null
@@ -1,120 +0,0 @@
-import type { BlockMDRule } from './type';
-
-const HEADING_REG_1 = /^(#{1,6}) +(.+)\n?/m;
-export const HeadingRule: BlockMDRule = {
-  match: (text) => text.match(HEADING_REG_1),
-  html: (match, parseInline) => {
-    const [, g1, g2] = match;
-    if (!g1 || !g2) return '';
-    const level = g1.length;
-    return `${parseInline ? parseInline(g2) : g2}`;
-  },
-};
-
-const CODEBLOCK_MD_1 = '```';
-const CODEBLOCK_REG_1 = /^`{3}(\S*)\n((?:.*\n)+?)`{3} *(?!.)\n?/m;
-export const CodeBlockRule: BlockMDRule = {
-  match: (text) => text.match(CODEBLOCK_REG_1),
-  html: (match) => {
-    const [, g1, g2] = match;
-    const classNameAtt = g1 ? ` class="language-${g1}"` : '';
-    return `
        ${g2}
        `;
-  },
-};
-
-const BLOCKQUOTE_MD_1 = '>';
-const QUOTE_LINE_PREFIX = /^> */;
-const BLOCKQUOTE_TRAILING_NEWLINE = /\n$/;
-const BLOCKQUOTE_REG_1 = /(^>.*\n?)+/m;
-export const BlockQuoteRule: BlockMDRule = {
-  match: (text) => text.match(BLOCKQUOTE_REG_1),
-  html: (match, parseInline) => {
-    const [blockquoteText] = match;
-
-    const lines = blockquoteText
-      .replace(BLOCKQUOTE_TRAILING_NEWLINE, '')
-      .split('\n')
-      .map((lineText) => {
-        const line = lineText.replace(QUOTE_LINE_PREFIX, '');
-        if (parseInline) return `${parseInline(line)}
        `;
-        return `${line}
        `;
-      })
-      .join('');
-    return `
        ${lines}
        `;
-  },
-};
-
-const ORDERED_LIST_MD_1 = '1.';
-const O_LIST_ITEM_PREFIX = /^([\da-zA-Z]\.) */;
-const O_LIST_START = /^([\d])\./;
-const O_LIST_TYPE = /^([aAiI])\./;
-const O_LIST_TRAILING_NEWLINE = /\n$/;
-const ORDERED_LIST_REG_1 = /(^(?:[\da-zA-Z]\.) +.+\n?)+/m;
-export const OrderedListRule: BlockMDRule = {
-  match: (text) => text.match(ORDERED_LIST_REG_1),
-  html: (match, parseInline) => {
-    const [listText] = match;
-    const [, listStart] = listText.match(O_LIST_START) ?? [];
-    const [, listType] = listText.match(O_LIST_TYPE) ?? [];
-
-    const lines = listText
-      .replace(O_LIST_TRAILING_NEWLINE, '')
-      .split('\n')
-      .map((lineText) => {
-        const line = lineText.replace(O_LIST_ITEM_PREFIX, '');
-        const txt = parseInline ? parseInline(line) : line;
-        return `
      • ${txt}
        • `;
-      })
-      .join('');
-
-    const dataMdAtt = `data-md="${listType || listStart || ORDERED_LIST_MD_1}"`;
-    const startAtt = listStart ? ` start="${listStart}"` : '';
-    const typeAtt = listType ? ` type="${listType}"` : '';
-    return `
          ${lines}
        `;
-  },
-};
-
-const UNORDERED_LIST_MD_1 = '-';
-const U_LIST_ITEM_PREFIX = /^[*-] */;
-const U_LIST_TRAILING_NEWLINE = /\n$/;
-const UNORDERED_LIST_REG_1 = /(^[*-] +.+\n?)+/m;
-export const UnorderedListRule: BlockMDRule = {
-  match: (text) => text.match(UNORDERED_LIST_REG_1),
-  html: (match, parseInline) => {
-    const [listText] = match;
-
-    const lines = listText
-      .replace(U_LIST_TRAILING_NEWLINE, '')
-      .split('\n')
-      .map((lineText) => {
-        const line = lineText.replace(U_LIST_ITEM_PREFIX, '');
-        const txt = parseInline ? parseInline(line) : line;
-        return `
      • ${txt}
        • `;
-      })
-      .join('');
-
-    return `
          ${lines}
        `;
-  },
-};
-
-const HR_MD = '---';
-const HR_REG = /^--- *(?:\n|$)/m;
-export const HorizontalRuleRule: BlockMDRule = {
-  match: (text) => text.match(HR_REG),
-  html: () => `
        `,
-};
-
-const SMALL_MD = '-#';
-const SMALL_REG = /^-# +(.+)\n?/m;
-export const SmallRule: BlockMDRule = {
-  match: (text) => text.match(SMALL_REG),
-  html: (match, parseInline) => {
-    const [, g1] = match;
-    if (!g1) return '';
-    const content = parseInline ? parseInline(g1) : g1;
-    return `${content}`;
-  },
-};
-
-export const UN_ESC_BLOCK_SEQ = /^\\*(#{1,6} +|```|>|([\da-zA-Z]\.) +|[*-] +|-# +|--- *)/;
-export const ESC_BLOCK_SEQ = /^\\(\\*(#{1,6} +|```|>|([\da-zA-Z]\.) +|[*-] +|-# +|--- *))/;
diff --git a/src/app/plugins/markdown/block/runner.ts b/src/app/plugins/markdown/block/runner.ts
deleted file mode 100644
index ecaee874d..000000000
--- a/src/app/plugins/markdown/block/runner.ts
+++ /dev/null
@@ -1,25 +0,0 @@
-import { replaceMatch } from '$plugins/markdown/internal';
-import type { BlockMDParser, BlockMDRule } from './type';
-
-/**
- * Parses block-level markdown text into HTML using defined block rules.
- *
- * @param text - The text to parse.
- * @param rule - The markdown rule to run.
- * @param parse - A function that run the parser on remaining parts..
- * @param parseInline - Optional function to parse inline elements.
- * @returns The text with the markdown rule applied or `undefined` if no match is found.
- */
-export const runBlockRule = (
-  text: string,
-  rule: BlockMDRule,
-  parse: BlockMDParser,
-  parseInline?: (txt: string) => string
-): string | undefined => {
-  const matchResult = rule.match(text);
-  if (matchResult) {
-    const content = rule.html(matchResult, parseInline);
-    return replaceMatch(text, matchResult, content, (txt) => [parse(txt, parseInline)]).join('');
-  }
-  return undefined;
-};
diff --git a/src/app/plugins/markdown/block/type.ts b/src/app/plugins/markdown/block/type.ts
deleted file mode 100644
index dc272de83..000000000
--- a/src/app/plugins/markdown/block/type.ts
+++ /dev/null
@@ -1,30 +0,0 @@
-import type { MatchResult, MatchRule } from '$plugins/markdown/internal';
-
-/**
- * Type for a function that parses block-level markdown into HTML.
- *
- * @param text - The markdown text to be parsed.
- * @param parseInline - Optional function to parse inline elements.
- * @returns The parsed HTML.
- */
-export type BlockMDParser = (text: string, parseInline?: (txt: string) => string) => string;
-
-/**
- * Type for a function that converts a block match to output.
- *
- * @param match - The match result.
- * @param parseInline - Optional function to parse inline elements.
- * @returns The output string after processing the match.
- */
-export type BlockMatchConverter = (
-  match: MatchResult,
-  parseInline?: (txt: string) => string
-) => string;
-
-/**
- * Type representing a block-level markdown rule that includes a matching pattern and HTML conversion.
- */
-export type BlockMDRule = {
-  match: MatchRule; // A function that matches a specific markdown pattern.
-  html: BlockMatchConverter; // A function that converts the match to HTML.
-};
diff --git a/src/app/plugins/markdown/extensions/matrix-emoticon.ts b/src/app/plugins/markdown/extensions/matrix-emoticon.ts
new file mode 100644
index 000000000..a340358b5
--- /dev/null
+++ b/src/app/plugins/markdown/extensions/matrix-emoticon.ts
@@ -0,0 +1,68 @@
+import type { TokenizerExtension, RendererExtension } from 'marked';
+
+/**
+ * Validates that a URL is a proper mxc:// URI.
+ * Returns true if valid, false otherwise.
+ */
+function validateMxcUrlInternal(url: string): boolean {
+  if (!url.startsWith('mxc://')) return false;
+
+  try {
+    const parsed = new URL(url);
+    if (parsed.protocol !== 'mxc:') return false;
+    if (!parsed.host) return false;
+    if (!parsed.pathname || parsed.pathname.length < 1) return false;
+    if (parsed.username || parsed.password || parsed.search || parsed.hash) return false;
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+// Extension to preserve img[data-mx-emoticon] tags through markdown pipeline
+export const matrixEmoticonExtension = {
+  name: 'emoticon',
+  level: 'inline',
+  start(src: string) {
+    return src.indexOf('data-mx-emoticon');
+  },
+  tokenizer(src: string) {
+    const rule = /^]*data-mx-emoticon[^>]*(?:\/>|>(?=\s*<\/img>))/i;
+    const match = rule.exec(src);
+    if (!match) return undefined;
+
+    const rawHtml = match[0];
+
+    const srcMatch = /src\s*=\s*["']([^"']*)["']/i.exec(rawHtml);
+    if (!srcMatch) return undefined;
+
+    const srcValue = srcMatch[1];
+    if (!srcValue || !validateMxcUrlInternal(srcValue)) return undefined;
+
+    return {
+      type: 'emoticon',
+      raw: rawHtml,
+      html: rawHtml,
+    };
+  },
+  renderer(token) {
+    return token.html;
+  },
+} satisfies TokenizerExtension & RendererExtension;
+
+// Preprocessor to strip invalid emoticon img tags before marked processing
+export function preprocessEmoticon(markdown: string): string {
+  // Remove img[data-mx-emoticon] tags with invalid src URLs
+  return markdown.replace(/]*data-mx-emoticon[^>]*>/gi, (tag) => {
+    const srcMatch = /src\s*=\s*["']([^"']*)["']/i.exec(tag);
+    if (!srcMatch) return tag; // Keep if no src attribute
+    const srcValue = srcMatch[1];
+    if (!srcValue || !validateMxcUrlInternal(srcValue)) return ''; // Remove invalid
+    return tag; // Keep valid
+  });
+}
+
+// Standalone validation function for use by htmlToMarkdown
+export function validateMxcUrl(url: string): boolean {
+  return validateMxcUrlInternal(url);
+}
diff --git a/src/app/plugins/markdown/extensions/matrix-math.ts b/src/app/plugins/markdown/extensions/matrix-math.ts
new file mode 100644
index 000000000..590d84b55
--- /dev/null
+++ b/src/app/plugins/markdown/extensions/matrix-math.ts
@@ -0,0 +1,55 @@
+import type { TokenizerExtension, RendererExtension } from 'marked';
+
+function escapeHtml(text: string): string {
+  return text
+    .replace(/&/g, '&')
+    .replace(//g, '>')
+    .replace(/"/g, '"');
+}
+
+// Inline math: $...$
+export const matrixMathExtension = {
+  name: 'math',
+  level: 'inline',
+  start(src: string) {
+    return src.indexOf('$');
+  },
+  tokenizer(src: string) {
+    const match = /^\$([^$]+)\$/.exec(src);
+    if (match) {
+      return {
+        type: 'math',
+        raw: match[0],
+        latex: match[1],
+      };
+    }
+    return undefined;
+  },
+  renderer(token) {
+    return `${token.latex}`;
+  },
+} satisfies TokenizerExtension & RendererExtension;
+
+// Block math: $$...$$
+export const matrixMathBlockExtension = {
+  name: 'mathBlock',
+  level: 'block',
+  start(src: string) {
+    return src.indexOf('$$');
+  },
+  tokenizer(src: string) {
+    const match = /^\$\$([^$]+)\$\$\n?/.exec(src);
+    if (match) {
+      return {
+        type: 'mathBlock',
+        raw: match[0],
+        latex: match[1]?.trim() ?? '',
+      };
+    }
+    return undefined;
+  },
+  renderer(token) {
+    return `
        ${token.latex}
        `;
+  },
+} satisfies TokenizerExtension & RendererExtension;
diff --git a/src/app/plugins/markdown/extensions/matrix-spoiler.ts b/src/app/plugins/markdown/extensions/matrix-spoiler.ts
new file mode 100644
index 000000000..30bc2cba4
--- /dev/null
+++ b/src/app/plugins/markdown/extensions/matrix-spoiler.ts
@@ -0,0 +1,37 @@
+import type { TokenizerExtension, RendererExtension, Tokens } from 'marked';
+
+// Extend marked's lexer to handle ||spoiler|| syntax
+export const matrixSpoilerExtension = {
+  name: 'spoiler',
+  level: 'inline',
+  start(src: string) {
+    return src.indexOf('||');
+  },
+  tokenizer(
+    this: { lexer: { inlineTokens: (t: string, tokens: Tokens.Generic[]) => void } },
+    src: string
+  ) {
+    // Only match if || at the very start of the remaining text
+    if (!src.startsWith('||')) return undefined;
+    const rule = /^\|\|(.+?)\|\|/;
+    const match = rule.exec(src);
+    if (match) {
+      const token = {
+        type: 'spoiler',
+        raw: match[0],
+        text: match[1],
+        tokens: [] as Tokens.Generic[],
+      };
+      this.lexer.inlineTokens(token.text!, token.tokens);
+      return token;
+    }
+    return undefined;
+  },
+  renderer(
+    this: { parser: { parseInline: (tokens: Tokens.Generic[]) => string } },
+    token: Tokens.Generic
+  ) {
+    const tokens = (token as { tokens: Tokens.Generic[] }).tokens || [];
+    return `${this.parser.parseInline(tokens)}`;
+  },
+} satisfies TokenizerExtension & RendererExtension;
diff --git a/src/app/plugins/markdown/extensions/matrix-subscript.ts b/src/app/plugins/markdown/extensions/matrix-subscript.ts
new file mode 100644
index 000000000..922f9377d
--- /dev/null
+++ b/src/app/plugins/markdown/extensions/matrix-subscript.ts
@@ -0,0 +1,34 @@
+import type { TokenizerExtension, RendererExtension, Tokens } from 'marked';
+
+// Subscript extension: -# text (Matrix spec small/sub tag)
+export const matrixSubscriptExtension = {
+  name: 'subscript',
+  level: 'block',
+  start(src: string) {
+    return src.indexOf('-#');
+  },
+  tokenizer(
+    this: { lexer: { inlineTokens: (t: string, tokens: Tokens.Generic[]) => void } },
+    src: string
+  ) {
+    const match = /^-# +(.+)/.exec(src);
+    if (match) {
+      const token = {
+        type: 'subscript',
+        raw: match[0],
+        text: match[1],
+        tokens: [] as Tokens.Generic[],
+      };
+      this.lexer.inlineTokens(token.text!, token.tokens);
+      return token;
+    }
+    return undefined;
+  },
+  renderer(
+    this: { parser: { parseInline: (tokens: Tokens.Generic[]) => string } },
+    token: Tokens.Generic
+  ) {
+    const tokens = (token as { tokens: Tokens.Generic[] }).tokens || [];
+    return `${this.parser.parseInline(tokens)}`;
+  },
+} satisfies TokenizerExtension & RendererExtension;
diff --git a/src/app/plugins/markdown/extensions/matrix.test.ts b/src/app/plugins/markdown/extensions/matrix.test.ts
new file mode 100644
index 000000000..ed1b254a8
--- /dev/null
+++ b/src/app/plugins/markdown/extensions/matrix.test.ts
@@ -0,0 +1,74 @@
+import { describe, expect, it } from 'vitest';
+import { marked } from 'marked';
+import { matrixSpoilerExtension } from './matrix-spoiler';
+import { matrixMathExtension, matrixMathBlockExtension } from './matrix-math';
+import { matrixSubscriptExtension } from './matrix-subscript';
+
+function parse(input: string): string {
+  const processor = marked.use({
+    extensions: [
+      matrixSpoilerExtension,
+      matrixMathExtension,
+      matrixMathBlockExtension,
+      matrixSubscriptExtension,
+    ],
+  });
+  return processor.parse(input) as string;
+}
+
+describe('matrixSpoilerExtension', () => {
+  it('parses ||spoiler|| syntax', () => {
+    expect(parse('Hello ||spoiler|| world')).toContain('data-mx-spoiler');
+    expect(parse('Hello ||spoiler|| world')).toContain('>spoiler<');
+  });
+
+  it('does not parse text without spoiler markers', () => {
+    expect(parse('No spoilers here')).not.toContain('data-mx-spoiler');
+  });
+
+  it('parses ||hidden|| without surrounding text', () => {
+    const result = parse('||hidden||');
+    expect(result).toContain('data-mx-spoiler');
+    expect(result).toContain('>hidden<');
+  });
+});
+
+describe('matrixMathExtension (inline)', () => {
+  it('parses inline $...$ syntax', () => {
+    expect(parse('$E = mc^2$')).toContain('data-mx-maths');
+    expect(parse('$E = mc^2$')).toContain('E = mc^2');
+  });
+
+  it('parses inline math within text', () => {
+    const result = parse('Math: $x$ value');
+    expect(result).toContain('data-mx-maths');
+    expect(result).toContain('>x<');
+  });
+
+  it('does not parse unmatched $', () => {
+    expect(parse('No $ math here')).not.toContain('data-mx-maths');
+  });
+});
+
+describe('matrixMathBlockExtension (block)', () => {
+  it('parses block $$...$$ syntax', () => {
+    const result = parse('$$\\frac{a}{b}$$');
+    expect(result).toContain('data-mx-maths');
+    expect(result).toContain(' {
+    const result = parse('$x$');
+    expect(result).not.toContain(' {
+  it('parses -# syntax', () => {
+    const result = parse('-# subscript text');
+    expect(result).toContain(' {
+  it('converts headings', () => {
+    expect(htmlToMarkdown('
        Hello
        ')).toContain('# Hello');
+    expect(htmlToMarkdown('
        World
        ')).toContain('## World');
+  });
+
+  it('converts bold text', () => {
+    expect(htmlToMarkdown('bold')).toContain('**bold**');
+    expect(htmlToMarkdown('bold')).toContain('**bold**');
+  });
+
+  it('converts italic text', () => {
+    expect(htmlToMarkdown('italic')).toContain('*italic*');
+    expect(htmlToMarkdown('italic')).toContain('*italic*');
+  });
+
+  it('converts strikethrough', () => {
+    expect(htmlToMarkdown('deleted')).toContain('~~deleted~~');
+    expect(htmlToMarkdown('deleted')).toContain('~~deleted~~');
+  });
+
+  it('converts inline code', () => {
+    expect(htmlToMarkdown('code')).toContain('`code`');
+  });
+
+  it('converts code blocks', () => {
+    expect(htmlToMarkdown('
        fn main() {}
        ')).toContain(
+      '```rust'
+    );
+  });
+
+  it('converts links', () => {
+    expect(htmlToMarkdown('link')).toContain(
+      '[link](https://example.com)'
+    );
+  });
+
+  it('converts spoiler spans', () => {
+    expect(htmlToMarkdown('hidden')).toContain('||hidden||');
+  });
+
+  it('converts inline math spans', () => {
+    expect(htmlToMarkdown('E = mc^2')).toContain(
+      '$E = mc^2$'
+    );
+  });
+
+  it('converts block math divs', () => {
+    expect(htmlToMarkdown('
        frac
        ')).toContain(
+      '$$\\frac{a}{b}$$'
+    );
+  });
+
+  it('converts blockquotes', () => {
+    const result = htmlToMarkdown('
        Quote text
        ');
+    expect(result).toContain('>');
+    expect(result).toContain('Quote text');
+  });
+
+  it('converts unordered lists', () => {
+    const result = htmlToMarkdown('
        • Item 1
        • Item 2
        ');
+    expect(result).toContain('-');
+    expect(result).toContain('Item 1');
+  });
+
+  it('converts ordered lists', () => {
+    const result = htmlToMarkdown('
        1. Item 1
        2. Item 2
        ');
+    expect(result).toContain('1.');
+    expect(result).toContain('Item 1');
+  });
+
+  it('preserves data-md attributes for round-trip', () => {
+    const result = htmlToMarkdown('bold');
+    expect(result).toContain('**bold**');
+  });
+
+  it('escapes markdown special characters in text', () => {
+    const result = htmlToMarkdown('
        Hello *world*
        ');
+    expect(result).toContain('\\*');
+  });
+});
diff --git a/src/app/plugins/markdown/htmlToMarkdown.ts b/src/app/plugins/markdown/htmlToMarkdown.ts
new file mode 100644
index 000000000..f6835a1dc
--- /dev/null
+++ b/src/app/plugins/markdown/htmlToMarkdown.ts
@@ -0,0 +1,348 @@
+import parse from 'html-dom-parser';
+import type { ChildNode, Element } from 'domhandler';
+import { isText, isTag } from 'domhandler';
+import { validateMxcUrl } from './extensions/matrix-emoticon';
+import { escapeMarkdownInlineSequences } from './utils';
+
+/**
+ * Converts Matrix-compatible HTML back to markdown for round-trip editing.
+ * Preserves original markdown syntax via data-md attributes and converts
+ * Matrix-specific elements (spoilers, math) back to their markdown equivalents.
+ *
+ * @param html - Input HTML string (should be pre-sanitized)
+ * @returns Markdown string for editor editing
+ */
+export function htmlToMarkdown(html: string): string {
+  const domNodes = parse(html);
+  return processNodes(domNodes).trim();
+}
+
+function isBlockTag(node: ChildNode | undefined): boolean {
+  if (!node || !isTag(node)) return false;
+  const blocks = [
+    'p',
+    'div',
+    'h1',
+    'h2',
+    'h3',
+    'h4',
+    'h5',
+    'h6',
+    'ul',
+    'ol',
+    'li',
+    'blockquote',
+    'pre',
+    'hr',
+    'table',
+    'details',
+    'summary',
+  ];
+  return blocks.includes(node.name.toLowerCase());
+}
+
+function processNodes(nodes: ChildNode[]): string {
+  return nodes
+    .filter((n, i) => {
+      if (isText(n) && /^\s*$/.test(n.data)) {
+        const prev = nodes[i - 1];
+        const next = nodes[i + 1];
+        // Ignore whitespace between block tags or at the edges
+        const isBetweenBlocks = (!prev || isBlockTag(prev)) && (!next || isBlockTag(next));
+        if (isBetweenBlocks) return false;
+      }
+      return true;
+    })
+    .map((n) => processNode(n))
+    .join('');
+}
+
+function processNode(node: ChildNode, listDepth: number = 0): string {
+  if (isText(node)) {
+    return escapeMarkdownInlineSequences(node.data);
+  }
+
+  if (!isTag(node)) {
+    return '';
+  }
+
+  const tag = node.name.toLowerCase();
+
+  // Handle Matrix-specific attributes
+  if (tag === 'span') {
+    if (node.attribs['data-mx-spoiler'] !== undefined) {
+      return processSpoiler(node);
+    }
+    if (node.attribs['data-mx-maths'] !== undefined) {
+      return processMath(node, 'inline');
+    }
+    if (node.attribs['data-md'] !== undefined) {
+      return processInlineMarkdown(node);
+    }
+    if (
+      node.attribs['data-mx-color'] !== undefined ||
+      node.attribs['data-mx-bg-color'] !== undefined
+    ) {
+      return reconstructTag(node);
+    }
+  }
+
+  if (tag === 'div') {
+    if (node.attribs['data-mx-maths'] !== undefined) {
+      return processMath(node, 'block');
+    }
+  }
+
+  // Handle block elements
+  switch (tag) {
+    case 'h1':
+    case 'h2':
+    case 'h3':
+    case 'h4':
+    case 'h5':
+    case 'h6':
+      return processHeading(node, tag);
+
+    case 'p':
+      return processParagraph(node);
+
+    case 'strong':
+    case 'b':
+      return processInlineWrapper(node, '**');
+
+    case 'em':
+    case 'i':
+      return processInlineWrapper(node, '*');
+
+    case 'u':
+      return processInlineWrapper(node, '_');
+
+    case 's':
+    case 'del':
+      return processInlineWrapper(node, '~~');
+
+    case 'code':
+      return processCode(node);
+
+    case 'pre':
+      return processPre(node);
+
+    case 'blockquote':
+      return processBlockquote(node);
+
+    case 'ul':
+      return processUnorderedList(node, listDepth);
+
+    case 'ol':
+      return processOrderedList(node, listDepth);
+
+    case 'li':
+      return processListItem(node);
+
+    case 'a':
+      return processLink(node);
+
+    case 'br':
+      return '\n';
+
+    case 'hr':
+      return '---\n';
+
+    case 'sub':
+      return processSubscript(node);
+
+    case 'img':
+      return processImage(node);
+
+    default:
+      return processInlineElements(node);
+  }
+}
+function reconstructTag(node: Element): string {
+  const content = processInlineElements(node);
+  const attributes = Object.entries(node.attribs)
+    .map(([key, value]) => ` ${key}="${value}"`)
+    .join('');
+  return `<${node.name}${attributes}>${content}`;
+}
+
+function processInlineElements(node: Element): string {
+  return node.children.map((c) => processNode(c)).join('');
+}
+
+function processInlineWrapper(node: Element, marker: string): string {
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `${marker}${content}${marker}`;
+}
+
+function processCode(node: Element): string {
+  const codeContent = node.children.map((c) => processNode(c)).join('');
+
+  // Check if this is inside a pre (code block)
+  if (node.parent && isTag(node.parent) && node.parent.name === 'pre') {
+    return codeContent;
+  }
+
+  // Single backtick for inline code
+  return `\`${codeContent}\``;
+}
+
+function processPre(node: Element): string {
+  // Get language from class="language-xxx"
+  const codeChild = node.children.find((c): c is Element => isTag(c) && c.name === 'code');
+  const className = codeChild?.attribs.class ?? '';
+  const langMatch = className.match(/language-(\S+)/);
+  const lang = langMatch ? langMatch[1] : '';
+
+  const codeContent = codeChild
+    ? codeChild.children.map((c) => processNode(c)).join('')
+    : node.children.map((c) => processNode(c)).join('');
+
+  return `\`\`\`${lang}\n${codeContent}\`\`\`\n`;
+}
+
+function processHeading(node: Element, tag: string): string {
+  const level = tag.charAt(1);
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `${'#'.repeat(parseInt(level, 10))} ${content}\n`;
+}
+
+function processParagraph(node: Element): string {
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `${content}\n`;
+}
+
+function processBlockquote(node: Element): string {
+  const content = node.children
+    .map((child) => {
+      if (isTag(child) && child.name === 'br') return '\n';
+      const text = processNode(child);
+      return text.replace(/\n/g, '\n> ');
+    })
+    .join('');
+  return `> ${content}\n`;
+}
+
+/**
+ * Process children of a list item, separating inline content from nested lists.
+ * Nested lists are processed with increased depth for indentation.
+ */
+function processListItemChildren(li: Element, depth: number): string {
+  const inlineParts: string[] = [];
+  const nestedParts: string[] = [];
+
+  li.children.forEach((child) => {
+    if (isTag(child) && (child.name === 'ul' || child.name === 'ol')) {
+      // Nested list, process with increased depth
+      nestedParts.push(processNode(child, depth + 1));
+    } else if (isTag(child) && child.name === 'p') {
+      // Unwrap 
         inside 
      • 
+      inlineParts.push(child.children.map((c) => processNode(c)).join(''));
+    } else {
+      inlineParts.push(processNode(child));
+    }
+  });
+
+  let result = inlineParts.join('').trim();
+  if (nestedParts.length > 0) {
+    result += '\n' + nestedParts.join('').trimEnd();
+  }
+  return result;
+}
+
+function processUnorderedList(node: Element, depth: number = 0): string {
+  const mdSequence = node.attribs['data-md'] || '-';
+  const indent = '  '.repeat(depth);
+  const items = node.children
+    .filter((c): c is Element => isTag(c) && c.name === 'li')
+    .map((li) => {
+      const content = processListItemChildren(li, depth);
+      return `${indent}${mdSequence} ${content}`;
+    })
+    .join('\n');
+  return items + '\n';
+}
+
+function processOrderedList(node: Element, depth: number = 0): string {
+  const mdSequence = node.attribs['data-md'] || '1.';
+  const [starOrHyphen] = mdSequence.match(/^\*|-$/) ?? [];
+  const outPrefix = starOrHyphen
+    ? starOrHyphen
+    : mdSequence.endsWith('.')
+      ? mdSequence
+      : `${mdSequence}.`;
+
+  const indent = '  '.repeat(depth);
+  const items = node.children
+    .filter((c): c is Element => isTag(c) && c.name === 'li')
+    .map((li, index) => {
+      let currentPrefix = outPrefix;
+      if (!starOrHyphen) {
+        const start = parseInt(node.attribs.start || mdSequence, 10);
+        if (!isNaN(start)) {
+          currentPrefix = `${start + index}.`;
+        }
+      }
+      const content = processListItemChildren(li, depth);
+      return `${indent}${currentPrefix} ${content}`;
+    })
+    .join('\n');
+  return items + '\n';
+}
+
+function processListItem(node: Element): string {
+  const content = node.children
+    .map((child) => {
+      if (isTag(child) && child.name === 'p') {
+        return child.children.map((c) => processNode(c)).join('');
+      }
+      return processNode(child);
+    })
+    .join('');
+  return `- ${content}\n`;
+}
+
+function processSubscript(node: Element): string {
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `-# ${content}\n`;
+}
+
+function processLink(node: Element): string {
+  const href = node.attribs.href ?? '';
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `[${content}](${href})`;
+}
+
+function processSpoiler(node: Element): string {
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `||${content}||`;
+}
+
+function processMath(node: Element, mode: 'inline' | 'block'): string {
+  const latex = node.attribs['data-mx-maths'] ?? '';
+  if (mode === 'block') {
+    return `$$${latex}$$`;
+  }
+  return `$${latex}$`;
+}
+
+function processInlineMarkdown(node: Element): string {
+  const mdSequence = node.attribs['data-md'] ?? '';
+  const content = node.children.map((c) => processNode(c)).join('');
+  return `${mdSequence}${content}${mdSequence}`;
+}
+
+function processImage(node: Element): string {
+  if (node.attribs['data-mx-emoticon'] === undefined) {
+    return '';
+  }
+
+  const src = node.attribs.src ?? '';
+  const alt = node.attribs.alt ?? '';
+
+  if (!validateMxcUrl(src)) {
+    return '';
+  }
+
+  return `${alt}`;
+}
diff --git a/src/app/plugins/markdown/index.ts b/src/app/plugins/markdown/index.ts
index 4c4e4491a..36613095f 100644
--- a/src/app/plugins/markdown/index.ts
+++ b/src/app/plugins/markdown/index.ts
@@ -1,3 +1,3 @@
 export * from './utils';
-export * from './block';
-export * from './inline';
+export { markdownToHtml } from './markdownToHtml';
+export { htmlToMarkdown, injectDataMd } from './markdownPipeline';
diff --git a/src/app/plugins/markdown/injectDataMd.test.ts b/src/app/plugins/markdown/injectDataMd.test.ts
new file mode 100644
index 000000000..2572c9e20
--- /dev/null
+++ b/src/app/plugins/markdown/injectDataMd.test.ts
@@ -0,0 +1,81 @@
+import { describe, expect, it } from 'vitest';
+import { injectDataMd } from './injectDataMd';
+
+describe('injectDataMd', () => {
+  it('injects data-md into headings', () => {
+    const result = injectDataMd('
        Hello
        ');
+    expect(result).toContain('data-md="#');
+  });
+
+  it('does not inject data-md if already present', () => {
+    const result = injectDataMd('
        Hello
        ');
+    expect(result).toContain('data-md="#');
+    // Should not have duplicate data-md
+    expect(result.match(/data-md="#/g) ?? []).toHaveLength(1);
+  });
+
+  it('injects data-md into blockquotes', () => {
+    const result = injectDataMd('
        Quote
        ');
+    expect(result).toContain('data-md=">"');
+  });
+
+  it('injects data-md into code blocks', () => {
+    const result = injectDataMd('
        code
        ');
+    expect(result).toContain('data-md="```"');
+  });
+
+  it('injects data-md into horizontal rules', () => {
+    const result = injectDataMd('
        ');
+    expect(result).toContain('data-md="---"');
+  });
+
+  it('injects data-md into subscript', () => {
+    const result = injectDataMd('text');
+    expect(result).toContain('data-md="-#"');
+  });
+
+  it('injects data-md into unordered lists', () => {
+    const result = injectDataMd('
        • Item
        ');
+    expect(result).toContain('data-md="-"');
+  });
+
+  it('injects data-md into ordered lists', () => {
+    const result = injectDataMd('
        1. Item
        ');
+    expect(result).toContain('data-md="1."');
+  });
+
+  it('injects data-md into strong tags', () => {
+    const result = injectDataMd('bold');
+    expect(result).toContain('data-md="**"');
+  });
+
+  it('injects data-md into em tags', () => {
+    const result = injectDataMd('italic');
+    expect(result).toContain('data-md="*"');
+  });
+
+  it('injects data-md into u tags', () => {
+    const result = injectDataMd('underline');
+    expect(result).toContain('data-md="_"');
+  });
+
+  it('injects data-md into s tags', () => {
+    const result = injectDataMd('strike');
+    expect(result).toContain('data-md="~~"');
+  });
+
+  it('injects data-md into del tags', () => {
+    const result = injectDataMd('deleted');
+    expect(result).toContain('data-md="~~"');
+  });
+
+  it('injects data-md into code tags', () => {
+    const result = injectDataMd('inline');
+    expect(result).toContain('data-md="`"');
+  });
+
+  it('handles multiline code blocks without injecting data-md', () => {
+    const result = injectDataMd('line1\nline2');
+    expect(result).not.toContain('data-md');
+  });
+});
diff --git a/src/app/plugins/markdown/injectDataMd.ts b/src/app/plugins/markdown/injectDataMd.ts
new file mode 100644
index 000000000..e27cfdb7b
--- /dev/null
+++ b/src/app/plugins/markdown/injectDataMd.ts
@@ -0,0 +1,100 @@
+/**
+ * Injects data-md attributes into HTML to preserve markdown syntax for round-trip editing.
+ * This is used when receiving HTML from a sender that may not have preserved data-md.
+ *
+ * The function identifies common HTML patterns and adds the appropriate data-md attribute
+ * so that when converting back to markdown, the original syntax is preserved.
+ *
+ * @param html - Input HTML string
+ * @returns HTML string with data-md attributes injected
+ */
+export function injectDataMd(html: string): string {
+  // Inject heading data-md (e.g., 
        )
+  html = html.replace(/]*)>/g, (_, level, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    const hashes = '#'.repeat(parseInt(level, 10));
+    return ``;
+  });
+
+  // Inject blockquote data-md
+  html = html.replace(/]*)>/g, (_, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    return `
        `;
+  });
+
+  // Inject code block data-md
+  html = html.replace(/]*)>]*)>/g, (_, preAttrs, codeAttrs) => {
+    if (preAttrs.includes('data-md')) return ``;
+    return `
        `;
+  });
+
+  // Inject horizontal rule data-md
+  html = html.replace(/]*)>/g, (_, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    return `
        `;
+  });
+
+  // Inject subscript data-md
+  html = html.replace(/]*)>/g, (_, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    return ``;
+  });
+
+  // Inject ordered list data-md
+  html = html.replace(/]*)>/g, (_, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    return `
          `;
+  });
+
+  // Inject unordered list data-md
+  html = html.replace(/]*)>/g, (_, attrs) => {
+    if (attrs.includes('data-md')) return ``;
+    return `