From e802da10758b3ca56151e0e22ce1088c9248dd7a Mon Sep 17 00:00:00 2001
From: Waleed <walif6@gmail.com>
Date: Thu, 9 Jul 2026 13:31:16 -0700
Subject: [PATCH] feat(rich-markdown-editor): round-trip gate, VSCode/style
 paste, highlight, block reorder (#5539)
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

* fix(rich-markdown-editor): tighten read-only gate for uppercase entities and orphan ref-defs

Two silent-corruption cases the idempotency probe can't see:

- The HTML-entity safe-list used a case-insensitive regex, so `&AMP;`/`&LT;`/`&GT;` were
  treated as the round-trippable canonical entities and let through as editable, but the
  serializer only round-trips the lowercase forms and mangles the uppercase ones. Make the
  safe-list case-sensitive.
- An unused link/image reference definition (`[x]: url` with no `[x]` reference) is dropped
  entirely on serialize, a deletion the idempotency probe misses. Detect orphan definitions
  and open read-only; used definitions still inline losslessly and stay editable. The use
  check tolerates bracket-internal padding (`[ x ]`), and GFM footnote definitions (`[^id]: …`)
  are excluded since they round-trip verbatim.

* feat(rich-markdown-editor): VSCode code paste and strip <style>/<script> from pasted HTML

- Code copied from VSCode carries a `vscode-editor-data` payload with the source language,
  but its text/html is per-token colored spans that ProseMirror flattens into plain
  paragraphs. Read the payload and paste a real fenced code block with the mapped language.
  markdown/plaintext modes resolve to no language and fall through, so markdown copied from
  VSCode still parses as rich content rather than a fenced block.
- Google Sheets and Word prepend a `<style>` block of CSS that PM's DOM parser walks into
  the document as literal text. Strip <style>/<script> in transformPastedHTML before parsing.
- Add a `==…==` inline-mark hint (allowing a lone interior `=`) so a plain-text paste of
  `==highlight==` routes through the markdown parser and becomes a highlight mark.

* feat(rich-markdown-editor): add highlight (==mark==) support

Adds a highlight mark rendered as <mark> and serialized to/from ==text== (Pandoc/Obsidian
syntax). A custom inline tokenizer parses ==text== (inner text parsed as inline markdown so
nested marks like ==**bold**== survive; the body allows a lone `=` so ==a=b== round-trips).
`==` cannot be encoded in the delimiter, so an appendTransaction guard strips the mark from
any text that ends up containing `==` (e.g. a toolbar highlight over a==b), keeping the text
and never emitting the corrupting ==a==b==. Comparison operators (x == y) stay literal.
Wired with an input rule, paste rule, Mod-Shift-H, a bubble-menu button, and themed <mark>
styling. Also locks in mark-stacking round-trips across contexts.

* feat(rich-markdown-editor): keyboard block reordering (Mod-Shift-Arrow)

Mod-Shift-ArrowUp/ArrowDown swaps the current top-level block with its neighbour, carrying
the caret at its original offset (newBefore + offset, no off-by-one), and no-ops at the
document edges. Exposed as moveBlockUp/moveBlockDown commands (the keyboard shortcuts call
them). Pure UI interaction, no schema change. Covered by tests (order, caret offset, edge
no-op, list stays intact).
---
 .../rich-markdown-editor/block-mover.ts       |  94 ++++++++++++++++
 .../rich-markdown-editor/editor-extensions.ts |   2 +
 .../rich-markdown-editor/extensions.ts        |   2 +
 .../rich-markdown-editor/highlight.ts         | 105 ++++++++++++++++++
 .../rich-markdown-editor/keymap.test.ts       |  70 ++++++++++++
 .../rich-markdown-editor/keymap.ts            |   3 +-
 .../markdown-paste.test.ts                    |  66 ++++++++++-
 .../rich-markdown-editor/markdown-paste.ts    |  58 ++++++++++
 .../menus/bubble-menu.tsx                     |   9 ++
 .../rich-markdown-editor.css                  |  14 +++
 .../round-trip-safety.test.ts                 |  12 ++
 .../rich-markdown-editor/round-trip-safety.ts |  50 ++++++++-
 .../rich-markdown-editor/round-trip.test.ts   |  67 +++++++++++
 13 files changed, 545 insertions(+), 7 deletions(-)
 create mode 100644 apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/block-mover.ts
 create mode 100644 apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/highlight.ts

diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/block-mover.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/block-mover.ts
new file mode 100644
index 0000000000..9c93017375
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/block-mover.ts
@@ -0,0 +1,94 @@
+import { Extension } from '@tiptap/core'
+import type { EditorState, Transaction } from '@tiptap/pm/state'
+import { TextSelection } from '@tiptap/pm/state'
+
+/** The position range of the depth-1 block containing the cursor, or null at the document root. */
+function currentTopLevelBlock(state: EditorState): { from: number; to: number } | null {
+  const { $from } = state.selection
+  if ($from.depth === 0) return null
+  return { from: $from.before(1), to: $from.after(1) }
+}
+
+/**
+ * Swaps the current top-level block with its neighbour in `direction`, keeping the caret on the moved
+ * block. Adjacent top-level blocks share a boundary position (no separator token between them), so the
+ * move is a single `replaceWith` of the two-block span with the pair reordered. No-ops (returns false)
+ * at the matching document edge or when the neighbour isn't a top-level block. `newBefore` is the moved
+ * block's new `before(1)` position; adding the caret's original offset (`selection.from - from`, also
+ * measured from `before(1)`) re-anchors the caret at the same spot within the block.
+ */
+function moveBlock(
+  state: EditorState,
+  dispatch: ((tr: Transaction) => void) | undefined,
+  direction: 'up' | 'down'
+): boolean {
+  const block = currentTopLevelBlock(state)
+  if (!block) return false
+  const { from, to } = block
+  const up = direction === 'up'
+
+  if (up ? from === 0 : to >= state.doc.content.size) return false
+  const $neighbour = state.doc.resolve(up ? from - 1 : to + 1)
+  if ($neighbour.depth === 0) return false
+  if (!dispatch) return true
+
+  const spanFrom = up ? $neighbour.before(1) : from
+  const spanTo = up ? to : $neighbour.after(1)
+  const moving = state.doc.slice(from, to).content
+  const neighbour = up
+    ? state.doc.slice(spanFrom, from).content
+    : state.doc.slice(to, spanTo).content
+  const tr = state.tr.replaceWith(
+    spanFrom,
+    spanTo,
+    up ? moving.append(neighbour) : neighbour.append(moving)
+  )
+
+  const newBefore = up ? spanFrom : spanFrom + neighbour.size
+  const offset = state.selection.from - from
+  tr.setSelection(
+    TextSelection.near(tr.doc.resolve(Math.min(newBefore + offset, newBefore + moving.size)))
+  )
+  dispatch(tr.scrollIntoView())
+  return true
+}
+
+declare module '@tiptap/core' {
+  interface Commands<ReturnType> {
+    blockMover: {
+      /** Move the current top-level block up one position, carrying the caret. */
+      moveBlockUp: () => ReturnType
+      /** Move the current top-level block down one position, carrying the caret. */
+      moveBlockDown: () => ReturnType
+    }
+  }
+}
+
+/**
+ * Reorders the current top-level block with `Mod-Shift-ArrowUp`/`ArrowDown` — the standard
+ * keyboard block-move affordance (Notion/Obsidian). Pure UI interaction: no schema change, and the
+ * caret rides along with the block. A no-op (returns false, falling through) at the document edges.
+ */
+export const BlockMover = Extension.create({
+  name: 'blockMover',
+
+  addCommands() {
+    return {
+      moveBlockUp:
+        () =>
+        ({ state, dispatch }) =>
+          moveBlock(state, dispatch, 'up'),
+      moveBlockDown:
+        () =>
+        ({ state, dispatch }) =>
+          moveBlock(state, dispatch, 'down'),
+    }
+  },
+
+  addKeyboardShortcuts() {
+    return {
+      'Mod-Shift-ArrowUp': ({ editor }) => editor.commands.moveBlockUp(),
+      'Mod-Shift-ArrowDown': ({ editor }) => editor.commands.moveBlockDown(),
+    }
+  },
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/editor-extensions.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/editor-extensions.ts
index 01a2e2c82d..601d702c07 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/editor-extensions.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/editor-extensions.ts
@@ -1,5 +1,6 @@
 import type { Extensions } from '@tiptap/core'
 import Placeholder from '@tiptap/extension-placeholder'
+import { BlockMover } from './block-mover'
 import { CodeBlockWithLanguage } from './code-block'
 import { CodeBlockHighlight } from './code-highlight'
 import { LinkEmbed } from './embed/link-embed'
@@ -44,6 +45,7 @@ export function createMarkdownEditorExtensions({
     SlashCommand,
     Mention,
     RichMarkdownKeymap,
+    BlockMover,
     MarkdownPaste,
     Placeholder.configure({ placeholder }),
     ...(embeds ? [LinkEmbed] : []),
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/extensions.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/extensions.ts
index bf91dfd2cd..52e4731f27 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/extensions.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/extensions.ts
@@ -12,6 +12,7 @@ import {
 import { Markdown } from '@tiptap/markdown'
 import StarterKit from '@tiptap/starter-kit'
 import { MarkdownCodeBlock } from './code-block'
+import { Highlight } from './highlight'
 import { MarkdownImage } from './image'
 import { MarkdownLinkInputRule } from './link-input-rule'
 import { MarkdownMention } from './mention/mention-node'
@@ -130,6 +131,7 @@ export function createMarkdownContentExtensions(nodeViews: ContentNodeViews = {}
     }),
     BlockSafeParagraph,
     InlineCode,
+    Highlight,
     codeBlock,
     (nodeViews.image ?? MarkdownImage).configure({ allowBase64: true }),
     nodeViews.mention ?? MarkdownMention,
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/highlight.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/highlight.ts
new file mode 100644
index 0000000000..948b75127f
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/highlight.ts
@@ -0,0 +1,105 @@
+import type {
+  JSONContent,
+  MarkdownParseHelpers,
+  MarkdownRendererHelpers,
+  MarkdownToken,
+} from '@tiptap/core'
+import { Mark, markInputRule, markPasteRule, mergeAttributes } from '@tiptap/core'
+import type { Transaction } from '@tiptap/pm/state'
+import { Plugin } from '@tiptap/pm/state'
+
+/**
+ * `==text==` with non-space edges — the Pandoc/Obsidian highlight syntax. The body allows a lone `=`
+ * (`=(?!=)`) but never `==`, so a highlight over text containing `=` (e.g. `==a=b==`) round-trips while
+ * the closing `==` still terminates the run.
+ */
+const HIGHLIGHT_BODY = String.raw`(?:[^=]|=(?!=))+?`
+const HIGHLIGHT_TOKEN = new RegExp(String.raw`^==(?!\s)(${HIGHLIGHT_BODY})(?<!\s)==`)
+/** Input/paste rule form (anchored on a preceding boundary) so typing `==x==` toggles the mark. */
+const HIGHLIGHT_INPUT = new RegExp(String.raw`(?:^|\s)(==(?!\s)(${HIGHLIGHT_BODY})(?<!\s)==)$`)
+const HIGHLIGHT_PASTE = new RegExp(String.raw`(?:^|\s)(==(?!\s)(${HIGHLIGHT_BODY})(?<!\s)==)`, 'g')
+
+/**
+ * Highlight mark (`<mark>`), serialized to and parsed from `==text==`. CommonMark/`marked` has no
+ * highlight token, so this registers a custom inline tokenizer (parsing the inner text as inline
+ * markdown so nested marks like `==**bold**==` survive) and a `renderMarkdown` that wraps the content
+ * in `==`. Mirrors the verbatim-node registration pattern in `./raw-markdown-snippet`.
+ *
+ * The tokenizer's `start` returns the index of the next `==` (a plain string search, not the
+ * `createLexer()`-calling form the `RawHtmlBlock` caveat warns against) so `marked` breaks its inline
+ * text run there and gives this tokenizer a chance mid-line — `=` is not a default break char like `[`.
+ *
+ * A lone `=` is allowed inside a highlight (so `==a=b==` round-trips), but `==` cannot be encoded in the
+ * `==…==` delimiter (emitting `==a==b==` would split the highlight and corrupt the text on reload). The
+ * tokenizer/input rules already exclude `==`; an `appendTransaction` guard removes the mark from any
+ * text that ends up containing `==` (e.g. a toolbar highlight over `a==b`), so the doc never holds an
+ * unrepresentable highlight and serialization stays lossless.
+ */
+export const Highlight = Mark.create({
+  name: 'highlight',
+
+  parseHTML() {
+    return [{ tag: 'mark' }]
+  },
+
+  renderHTML({ HTMLAttributes }) {
+    return ['mark', mergeAttributes(HTMLAttributes), 0]
+  },
+
+  addInputRules() {
+    return [markInputRule({ find: HIGHLIGHT_INPUT, type: this.type })]
+  },
+
+  addPasteRules() {
+    return [markPasteRule({ find: HIGHLIGHT_PASTE, type: this.type })]
+  },
+
+  addKeyboardShortcuts() {
+    return { 'Mod-Shift-h': () => this.editor.commands.toggleMark(this.name) }
+  },
+
+  markdownTokenName: 'highlight',
+  markdownTokenizer: {
+    name: 'highlight',
+    level: 'inline' as const,
+    start: (src: string) => src.indexOf('=='),
+    tokenize(src: string): MarkdownToken | undefined {
+      const match = HIGHLIGHT_TOKEN.exec(src)
+      if (!match) return undefined
+      return { type: 'highlight', raw: match[0], text: match[1] }
+    },
+  },
+
+  parseMarkdown(token: MarkdownToken, helpers: MarkdownParseHelpers) {
+    const inner = token.text ?? ''
+    const tokens = helpers.tokenizeInline?.(inner)
+    const content = tokens ? helpers.parseInline(tokens) : [{ type: 'text', text: inner }]
+    return { mark: 'highlight', content }
+  },
+
+  renderMarkdown(node: JSONContent, h: MarkdownRendererHelpers) {
+    return `==${h.renderChildren(node.content ?? [])}==`
+  },
+
+  addProseMirrorPlugins() {
+    const markType = this.type
+    return [
+      new Plugin({
+        appendTransaction(transactions, _oldState, newState) {
+          if (!transactions.some((transaction) => transaction.docChanged)) return null
+          let tr: Transaction | null = null
+          newState.doc.descendants((node, pos) => {
+            if (
+              node.isText &&
+              node.text?.includes('==') &&
+              node.marks.some((mark) => mark.type === markType)
+            ) {
+              tr = (tr ?? newState.tr).removeMark(pos, pos + node.nodeSize, markType)
+            }
+          })
+          return tr
+        },
+      }),
+    ]
+  },
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.test.ts
index 1f12ca3b7e..862414f9fd 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.test.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.test.ts
@@ -257,3 +257,73 @@ describe('verbatim block boundary (isolating)', () => {
     }
   )
 })
+
+describe('block reordering (Mod-Shift-Arrow)', () => {
+  beforeEach(() => {
+    Element.prototype.scrollIntoView = vi.fn()
+  })
+
+  function caretInto(editor: Editor, word: string): void {
+    editor.state.doc.descendants((node, pos) => {
+      if (node.isText && node.text?.includes(word)) editor.commands.setTextSelection(pos + 1)
+    })
+  }
+
+  it('moves the current top-level block up, carrying the caret', () => {
+    const editor = editorWith('')
+    editor.commands.setContent('# One\n\nTwo para\n\n- item', { contentType: 'markdown' })
+    editor.commands.focus()
+    caretInto(editor, 'Two')
+    editor.commands.moveBlockUp()
+    expect(editor.getMarkdown().trim().startsWith('Two para')).toBe(true)
+    editor.destroy()
+  })
+
+  it('moves the current top-level block down', () => {
+    const editor = editorWith('')
+    editor.commands.setContent('# One\n\nTwo para', { contentType: 'markdown' })
+    editor.commands.focus()
+    caretInto(editor, 'One')
+    editor.commands.moveBlockDown()
+    expect(editor.getMarkdown().trim().startsWith('Two para')).toBe(true)
+    editor.destroy()
+  })
+
+  it.each([
+    ['up', '# One\n\nabcdef'],
+    ['down', 'abcdef\n\n# Two'],
+  ])('keeps the caret at its original offset after moving %s (no off-by-one)', (direction, md) => {
+    const editor = editorWith('')
+    editor.commands.setContent(md, { contentType: 'markdown' })
+    editor.commands.focus()
+    let textPos = -1
+    editor.state.doc.descendants((node, pos) => {
+      if (node.isText && node.text === 'abcdef') textPos = pos
+    })
+    editor.commands.setTextSelection(textPos + 3)
+    if (direction === 'up') editor.commands.moveBlockUp()
+    else editor.commands.moveBlockDown()
+    const at = editor.state.selection.from
+    expect(editor.state.doc.textBetween(at - 1, at)).toBe('c')
+    expect(editor.state.doc.textBetween(at, at + 1)).toBe('d')
+    editor.destroy()
+  })
+
+  it('is a no-op at the top edge and keeps a moved list intact', () => {
+    const top = editorWith('')
+    top.commands.setContent('# One\n\nTwo', { contentType: 'markdown' })
+    top.commands.focus()
+    caretInto(top, 'One')
+    top.commands.moveBlockUp()
+    expect(top.getMarkdown().trim().startsWith('# One')).toBe(true)
+    top.destroy()
+
+    const list = editorWith('')
+    list.commands.setContent('- a\n- b\n\npara', { contentType: 'markdown' })
+    list.commands.focus()
+    caretInto(list, 'para')
+    list.commands.moveBlockUp()
+    expect(list.getMarkdown().trim()).toBe('para\n\n- a\n- b')
+    list.destroy()
+  })
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.ts
index 6fb6ad4ac6..3034fd66fe 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/keymap.ts
@@ -128,7 +128,8 @@ function selectAdjacentSelectedLeaf(editor: Editor, direction: 'up' | 'down'): b
  *   same scoped behavior as a code editor.
  * - **ArrowUp/ArrowDown** select an adjacent divider or image, whether arrowing off a textblock edge
  *   ({@link selectAdjacentLeaf}) or stepping from one already-selected leaf to the next
- *   ({@link selectAdjacentSelectedLeaf}).
+ *   ({@link selectAdjacentSelectedLeaf}). (The `Mod-Shift-Arrow` block-reorder chords live separately
+ *   in `./block-mover.ts`.)
  *
  * Plus a plugin that (a) highlights dividers/images falling inside a range selection (e.g. select-all),
  * which the browser's native text highlight skips because leaves carry no text, and (b) flags the
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.test.ts
index b36857c037..9abccb28df 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.test.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.test.ts
@@ -21,10 +21,11 @@ function mount(editable = true): Editor {
 }
 
 /** Run the plugin paste handlers the way ProseMirror would, with a mocked clipboard. */
-function paste(ed: Editor, text: string, html = ''): boolean {
+function paste(ed: Editor, text: string, html = '', extra: Record<string, string> = {}): boolean {
   const event = {
     clipboardData: {
-      getData: (type: string) => (type === 'text/plain' ? text : type === 'text/html' ? html : ''),
+      getData: (type: string) =>
+        type === 'text/plain' ? text : type === 'text/html' ? html : (extra[type] ?? ''),
     },
   } as unknown as ClipboardEvent
   for (const plugin of ed.view.state.plugins) {
@@ -35,6 +36,16 @@ function paste(ed: Editor, text: string, html = ''): boolean {
   return false
 }
 
+/** Run the plugin `transformPastedHTML` chain the way ProseMirror would. */
+function transformHtml(ed: Editor, html: string): string {
+  let out = html
+  for (const plugin of ed.view.state.plugins) {
+    const fn = plugin.props?.transformPastedHTML
+    if (fn) out = fn.call(plugin.props, out, ed.view)
+  }
+  return out
+}
+
 describe('markdown paste', () => {
   it('renders a pasted inline link as a link mark', () => {
     editor = mount()
@@ -124,6 +135,8 @@ describe('markdown paste', () => {
     ['underscore italic', 'an _italic_ word', 'italic'],
     ['underscore bold', 'a __bold__ word', 'bold'],
     ['strikethrough', 'a ~~struck~~ word', 'strike'],
+    ['highlight', 'a ==marked== word', 'highlight'],
+    ['highlight with interior equals', 'x ==a=b== y', 'highlight'],
     ['inline code', 'some `code` here', 'code'],
     ['bullet list', '- one\n- two', 'bulletList'],
     ['ordered list', '1. one\n2. two', 'orderedList'],
@@ -178,4 +191,53 @@ describe('markdown paste', () => {
       .filter((type) => type !== 'paragraph')
     expect(structural).toEqual(['heading', 'bulletList', 'blockquote'])
   })
+
+  it('pastes VSCode code (vscode-editor-data) as a fenced code block with its language', () => {
+    editor = mount()
+    const code = 'const x: number = 1\nreturn x'
+    const handled = paste(editor, code, '<div><span>const</span></div>', {
+      'vscode-editor-data': JSON.stringify({ mode: 'typescript' }),
+    })
+    expect(handled).toBe(true)
+    const block = (editor.getJSON().content ?? []).find((n) => n.type === 'codeBlock')
+    expect(block).toBeDefined()
+    expect(block?.attrs?.language).toBe('typescript')
+    expect(block?.content?.[0]?.text).toBe(code)
+  })
+
+  it.each([
+    ['html', 'markup'],
+    ['shellscript', 'bash'],
+  ])('maps VSCode language id %s to our code-block value %s', (mode, expected) => {
+    editor = mount()
+    paste(editor, 'code', '', { 'vscode-editor-data': JSON.stringify({ mode }) })
+    const block = (editor.getJSON().content ?? []).find((n) => n.type === 'codeBlock')
+    expect(block?.attrs?.language).toBe(expected)
+  })
+
+  it.each(['markdown', 'md', 'mdx', 'plaintext'])(
+    'does NOT force a code block for VSCode %s copies (parses as markdown instead)',
+    (mode) => {
+      editor = mount()
+      const handled = paste(editor, '# Title\n\n- item', '', {
+        'vscode-editor-data': JSON.stringify({ mode }),
+      })
+      expect(handled).toBe(true)
+      const types = (editor.getJSON().content ?? []).map((n) => n.type)
+      expect(types).not.toContain('codeBlock')
+      expect(types).toContain('heading')
+      expect(types).toContain('bulletList')
+    }
+  )
+
+  it('strips <style>/<script> from pasted HTML so their text never leaks into the doc', () => {
+    editor = mount()
+    const gsheets =
+      '<google-sheets-html-origin><style>td{mso-1:2}</style><table><tr><td>a</td></tr></table></google-sheets-html-origin>'
+    const cleaned = transformHtml(editor, gsheets)
+    expect(cleaned).not.toContain('<style>')
+    expect(cleaned).not.toContain('mso-1')
+    expect(cleaned).toContain('<td>a</td>')
+    expect(transformHtml(editor, 'a<script>alert(1)</script>b')).toBe('ab')
+  })
 })
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.ts
index 88a9debbd9..83b829e50e 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/markdown-paste.ts
@@ -31,12 +31,61 @@ const INLINE_MARK_HINTS: ReadonlyArray<RegExp> = [
   /_[^_\n]+_/,
   /~~[^~\n]+~~/,
   /`[^`\n]+`/,
+  /==(?:[^=\n]|=(?!=))+==/,
 ]
 
 function hasAny(hints: ReadonlyArray<RegExp>, text: string): boolean {
   return hints.some((hint) => hint.test(text))
 }
 
+/**
+ * VSCode language ids that differ from our code-block language values. `markdown`/`plaintext` map to
+ * the empty string so they are NOT forced into a code block — markdown copied from VSCode should parse
+ * as markdown, and plain text should paste as text; other ids pass through as-is.
+ */
+const VSCODE_LANGUAGE_ALIASES: Readonly<Record<string, string>> = {
+  html: 'markup',
+  shellscript: 'bash',
+  shell: 'bash',
+  jsonc: 'json',
+  plaintext: '',
+  markdown: '',
+  md: '',
+  mdx: '',
+}
+
+/**
+ * Extracts the source language from VSCode's `vscode-editor-data` clipboard payload (a JSON blob with a
+ * `mode` field), mapping the few ids that differ from our code-block values. Returns `''` when the
+ * payload is absent, unparseable, or a non-code mode (plaintext/markdown). A real code language makes
+ * the paste handler emit a fenced code block — otherwise VSCode's per-token colored-span HTML would
+ * fall through to ProseMirror's default parser and flatten into plain paragraphs — while an empty
+ * result falls through so markdown copied from VSCode still parses as markdown.
+ */
+function parseVscodeLanguage(data: string | undefined): string {
+  if (!data) return ''
+  try {
+    const mode = (JSON.parse(data) as { mode?: unknown }).mode
+    if (typeof mode !== 'string') return ''
+    return VSCODE_LANGUAGE_ALIASES[mode] ?? mode
+  } catch {
+    return ''
+  }
+}
+
+/** `<style>`/`<script>` elements (with their content), matched as a pair via the tag backreference. */
+const NON_CONTENT_HTML = /<(style|script)\b[\s\S]*?<\/\1>/gi
+
+/**
+ * Strips `<style>`/`<script>` elements from pasted HTML. Google Sheets and Word prepend a `<style>`
+ * block of CSS (and Sheets a `<google-sheets-html-origin>` wrapper); ProseMirror's DOM parser has no
+ * rule for `<style>`, so it would walk the element's CSS text into the document as literal paragraphs.
+ * Removing these before parsing keeps the pasted content clean (PM already discards unknown wrappers).
+ */
+function stripNonContentHtml(html: string): string {
+  return html.replace(NON_CONTENT_HTML, '')
+}
+
 /**
  * Parses pasted plain text that looks like markdown into rich content, via the strict CommonMark
  * parser ({@link parseMarkdownToDoc}, `marked`). Pastes inside a code block or inline code are left
@@ -62,11 +111,20 @@ export const MarkdownPaste = Extension.create({
     return [
       new Plugin({
         props: {
+          transformPastedHTML: (html) => stripNonContentHtml(html),
           handlePaste: (_view, event) => {
             if (!editor.isEditable) return false
             if (editor.isActive('codeBlock') || editor.isActive('code')) return false
             const text = event.clipboardData?.getData('text/plain')
             if (!text) return false
+            const language = parseVscodeLanguage(event.clipboardData?.getData('vscode-editor-data'))
+            if (language) {
+              return editor.commands.insertContent({
+                type: 'codeBlock',
+                attrs: { language },
+                content: [{ type: 'text', text }],
+              })
+            }
             if (!hasAny(STRUCTURAL_MARKDOWN_HINTS, text)) {
               if (!hasAny(INLINE_MARK_HINTS, text)) return false
               if (event.clipboardData?.getData('text/html')) return false
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/menus/bubble-menu.tsx b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/menus/bubble-menu.tsx
index 0d4b1b397d..56b4dd7838 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/menus/bubble-menu.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/menus/bubble-menu.tsx
@@ -10,6 +10,7 @@ import {
   Code,
   Heading1,
   Heading2,
+  Highlighter,
   Italic,
   Link as LinkIcon,
   List,
@@ -76,6 +77,7 @@ export function EditorBubbleMenu({ editor, scrollContainerRef }: EditorBubbleMen
       bold: e.isActive('bold'),
       italic: e.isActive('italic'),
       strike: e.isActive('strike'),
+      highlight: e.isActive('highlight'),
       code: e.isActive('code'),
       link: e.isActive('link'),
       heading1: e.isActive('heading', { level: 1 }),
@@ -262,6 +264,13 @@ export function EditorBubbleMenu({ editor, scrollContainerRef }: EditorBubbleMen
             isActive={active.strike}
             onClick={() => editor.chain().focus().toggleStrike().run()}
           />
+          <ToolbarButton
+            icon={Highlighter}
+            label='Highlight'
+            shortcut='⌘⇧H'
+            isActive={active.highlight}
+            onClick={() => editor.chain().focus().toggleMark('highlight').run()}
+          />
           <ToolbarButton
             icon={Code}
             label='Code'
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
index 8c019c36f7..a5d5a82eee 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/rich-markdown-editor.css
@@ -397,6 +397,20 @@
   pointer-events: none;
 }
 
+/*
+ * Highlight mark (`==text==`). An opacity-based amber tint so it reads on both light and dark
+ * surfaces without a theme override; `color: inherit` keeps the text at the surrounding body color
+ * and `box-decoration-break: clone` keeps the tint clean where a highlight wraps across lines.
+ */
+.rich-markdown-prose mark {
+  background-color: rgba(255, 212, 0, 0.4);
+  color: inherit;
+  border-radius: 2px;
+  padding: 0 0.1em;
+  box-decoration-break: clone;
+  -webkit-box-decoration-break: clone;
+}
+
 /*
  * Field variant (modal embed): match the surrounding chip fields' typography exactly —
  * body at the chip `text-sm` (14px) scale and the placeholder at `--text-muted` (not the
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.test.ts
index c476e2f4df..d673091006 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.test.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.test.ts
@@ -55,6 +55,18 @@ describe('isRoundTripSafe', () => {
     expect(isRoundTripSafe('a&nbsp;b')).toBe(false)
     expect(isRoundTripSafe('a &amp; b &lt; c &gt; d')).toBe(true)
     expect(isRoundTripSafe('AT&T and R&D')).toBe(true)
+    expect(isRoundTripSafe('a &AMP; b')).toBe(false)
+    expect(isRoundTripSafe('a &LT; b &GT; c')).toBe(false)
+  })
+
+  it('rejects an orphan reference definition (serializer drops it) but allows used ones', () => {
+    expect(isRoundTripSafe('Some text.\n\n[unused]: https://example.com "title"')).toBe(false)
+    expect(isRoundTripSafe('[a]: u1\n[b]: u2\n\nuse only [a]')).toBe(false)
+    expect(isRoundTripSafe('See [x][1].\n\n[1]: https://example.com "T"')).toBe(true)
+    expect(isRoundTripSafe('A [shortcut] ref.\n\n[shortcut]: https://example.com')).toBe(true)
+    expect(isRoundTripSafe('Case [Foo] insensitive.\n\n[foo]: https://example.com')).toBe(true)
+    expect(isRoundTripSafe('A note.\n\n[^x]: the footnote body')).toBe(true)
+    expect(isRoundTripSafe('See [ foo ] here.\n\n[foo]: https://example.com')).toBe(true)
   })
 
   it('does not flag HTML/comments/entities inside tilde or nested code fences', () => {
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.ts
index 423669de7c..2e3dfe2ceb 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip-safety.ts
@@ -24,14 +24,16 @@ const PROBE_SIZE_LIMIT = 256 * 1024
  *   flattens `one<br>two` to `one two`. Matched on a table-shaped line (≥2 pipes) containing a `<br>`.
  * - **Hard break inside a heading** (trailing two spaces or a backslash) — the serializer splits
  *   the heading, ejecting the second line into a separate paragraph.
- * - **HTML entity** other than `&amp;`/`&lt;`/`&gt;` (e.g. `&copy;`, `&#39;`, `&nbsp;`) — the
- *   serializer escapes the `&`, turning the rendered character into literal entity source. A bare
- *   `&` with no `;` is left alone (it re-renders identically, so it's harmless churn).
+ * - **HTML entity** other than the lowercase canonical `&amp;`/`&lt;`/`&gt;` (e.g. `&copy;`, `&#39;`,
+ *   `&nbsp;`, or the uppercase `&AMP;`) — the serializer escapes the `&`, turning the rendered character
+ *   into literal entity source. The safe-list is deliberately case-*sensitive*: `@tiptap/markdown` only
+ *   round-trips the lowercase forms, so `&AMP;`/`&LT;`/`&GT;` must fall through to read-only rather than
+ *   be treated as safe. A bare `&` with no matching `;`-terminated name is left alone (harmless churn).
  */
 const STABLE_LOSS_PATTERNS: ReadonlyArray<RegExp> = [
   /^(?=(?:[^\n]*\|){2})[^\n]*<br\s*\/?>/im,
   /^#{1,6}\s.*(?: {2,}|\\)$/m,
-  /&(?!(?:amp|lt|gt);)(?:#x?[0-9a-f]+|[a-z][a-z0-9]*);/i,
+  /&(?!(?:amp|lt|gt);)(?:#x?[0-9a-fA-F]+|[a-zA-Z][a-zA-Z0-9]*);/,
 ]
 
 /**
@@ -60,6 +62,45 @@ function linkedImageCount(content: string): number {
   return content.match(LINKED_IMAGE_PATTERN)?.length ?? 0
 }
 
+/**
+ * A link/image reference definition line: `[label]: destination "optional title"` (up to 3 leading
+ * spaces). The `(?!\^)` excludes GFM footnote definitions (`[^id]: …`) — those are preserved verbatim
+ * by the footnote node and round-trip regardless of whether their reference is present, so they must
+ * not be treated as droppable orphan definitions.
+ */
+const REFERENCE_DEFINITION = /^ {0,3}\[(?!\^)([^\]]+)]:[ \t]+\S[^\n]*$/gm
+
+/** CommonMark reference labels match case-insensitively with internal whitespace collapsed. */
+function normalizeReferenceLabel(label: string): string {
+  return label.trim().replace(/\s+/g, ' ').toLowerCase()
+}
+
+/**
+ * True when `content` defines a link/image reference that nothing uses. A *used* reference inlines
+ * losslessly on serialize (`[x][id]` + `[id]: url` → `[x](url)`), but an *unused* definition is dropped
+ * entirely — a silent deletion the idempotency probe can't see (the drop happens on the first pass,
+ * which is then stable). We open such a file read-only rather than lose the definition on first edit.
+ * Conservative: a label counts as used if it appears bracketed anywhere in the body, so the rare
+ * inline-text collision errs toward editable, never toward a false read-only.
+ */
+function hasOrphanReferenceDefinition(content: string): boolean {
+  const labels = new Set<string>()
+  for (const match of content.matchAll(REFERENCE_DEFINITION)) {
+    labels.add(normalizeReferenceLabel(match[1]))
+  }
+  if (labels.size === 0) return false
+  const body = content
+    .replace(REFERENCE_DEFINITION, '')
+    .replace(/\s+/g, ' ')
+    .replace(/\[\s+/g, '[')
+    .replace(/\s+\]/g, ']')
+    .toLowerCase()
+  for (const label of labels) {
+    if (!body.includes(`[${label}]`)) return true
+  }
+  return false
+}
+
 /**
  * Whether `content` survives the editor's markdown round-trip without data loss or autosave
  * churn. The editor opens the content read-only when this is false, so the probe is deliberately
@@ -75,6 +116,7 @@ export function isRoundTripSafe(content: string): boolean {
   if (content.length > PROBE_SIZE_LIMIT) return false
   const stripped = stripCode(content)
   if (STABLE_LOSS_PATTERNS.some((pattern) => pattern.test(stripped))) return false
+  if (hasOrphanReferenceDefinition(stripped)) return false
   try {
     const once = serializeMarkdownDocument(content)
     if (linkedImageCount(stripped) !== linkedImageCount(stripCode(once))) return false
diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip.test.ts b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip.test.ts
index 1f8a9df6a1..eb6aa03a71 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip.test.ts
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/rich-markdown-editor/round-trip.test.ts
@@ -158,6 +158,23 @@ describe('editor markdown round-trip', () => {
     'bold code': '**`x`**',
     'heading strike code': '# ~~`x`~~',
     'table with pipe': '| x \\| y | 2 |\n| --- | --- |\n| a | b |',
+    'bold italic nested': '**bold _italic_ word**',
+    'strike bold nested': '~~**struck bold**~~',
+    'bold code inline': '**bold `code` here**',
+    'triple nested marks': '*i **b ~~s~~** i*',
+    'all marks in heading': '# **b** ~~s~~ *i* `c`',
+    'marks in bullet': '- **a** ~~b~~ `c`',
+    'marks in quote': '> **a** ~~b~~ *c*',
+    'nested list marks': '- **a**\n  - ~~b~~\n    - *c*',
+    'bold link': '[**bold link**](https://x.com)',
+    'link inside bold': '**see [x](https://x.com)**',
+    'table with marks': '| **b** | ~~s~~ | `c` |\n| --- | --- | --- |\n| *i* | a | b |',
+    'bold across code boundary': '**a** `b` **c**',
+    highlight: 'a ==marked== word',
+    'highlight in heading': '# a ==mark== b',
+    'highlight nested in bold': '**bold ==mark== here**',
+    'highlight in list': '- ==a== item',
+    'highlight with interior equals': 'x ==a=b== y',
   }
 
   for (const [name, input] of Object.entries(cases)) {
@@ -434,3 +451,53 @@ describe('consecutive empty paragraphs', () => {
     }
   )
 })
+
+describe('highlight ==mark==', () => {
+  function markPresent(src: string): boolean {
+    editor = new Editor({ extensions: createMarkdownContentExtensions() })
+    editor.commands.setContent(src, { contentType: 'markdown' })
+    const has = JSON.stringify(editor.getJSON()).includes('"type":"highlight"')
+    editor.destroy()
+    editor = null
+    return has
+  }
+
+  it('parses ==text== into a highlight mark, including mid-line and in headings', () => {
+    expect(markPresent('a ==marked== word')).toBe(true)
+    expect(markPresent('# a ==mark== b')).toBe(true)
+    expect(markPresent('**bold ==mark== here**')).toBe(true)
+  })
+
+  it('parses a highlight body containing a lone `=` (so ==a=b== round-trips)', () => {
+    expect(markPresent('x ==a=b== y')).toBe(true)
+  })
+
+  it('strips a highlight whose text contains `==` (unrepresentable), keeping the text', () => {
+    editor = new Editor({ extensions: createMarkdownContentExtensions() })
+    editor.commands.setContent('x a==b y', { contentType: 'markdown' })
+    let from = -1
+    let to = -1
+    editor.state.doc.descendants((node, pos) => {
+      if (node.isText) {
+        const i = node.text?.indexOf('a==b') ?? -1
+        if (i >= 0) {
+          from = pos + i
+          to = from + 4
+        }
+      }
+    })
+    editor.commands.setTextSelection({ from, to })
+    editor.commands.toggleMark('highlight')
+    const md = postProcessSerializedMarkdown(editor.getMarkdown())
+    expect(JSON.stringify(editor.getJSON())).not.toContain('"type":"highlight"')
+    expect(md).not.toContain('==a==b==')
+    expect(editor.getText().trim()).toBe('x a==b y')
+    editor.destroy()
+    editor = null
+  })
+
+  it('leaves comparison / spaced == operators as literal text', () => {
+    expect(markPresent('if x == y then z')).toBe(false)
+    expect(markPresent('a == b == c')).toBe(false)
+  })
+})