diff --git a/backlog/tasks/back-208 - Add-paste-as-markdown-support-in-Web-UI.md b/backlog/tasks/back-208 - Add-paste-as-markdown-support-in-Web-UI.md
index 3c4ce38aa..3f0c5a700 100644
--- a/backlog/tasks/back-208 - Add-paste-as-markdown-support-in-Web-UI.md	
+++ b/backlog/tasks/back-208 - Add-paste-as-markdown-support-in-Web-UI.md	
@@ -1,8 +1,9 @@
 ---
 id: BACK-208
 title: Add paste-as-markdown support in Web UI
-status: To Do
-assignee: []
+status: Done
+assignee:
+  - '@kimi'
 created_date: '2025-07-26'
 labels:
   - web-ui
@@ -14,17 +15,152 @@ priority: medium
 
 ## Description
 
-Implement automatic conversion of rich text content to markdown when pasting into task and document editors, allowing users to seamlessly paste content from Word, Google Docs, web pages, and other sources while maintaining proper markdown formatting
+Implement automatic conversion of rich text content to markdown when pasting into task and document editors, allowing users to seamlessly paste content from Word, Google Docs, web pages, and other sources while maintaining proper markdown formatting.
+
+**Phase 1 (Done):** Text, tables, lists, bold/italic/underline, links.
+**Phase 2 (Done):** Images — extract and save to `backlog/assets`, generate `![alt](/assets/...)` links.
 
 ## Acceptance Criteria
 
-- [ ] Rich text content pasted into task edit fields is automatically converted to markdown
-- [ ] Rich text content pasted into document edit pages is automatically converted to markdown
-- [ ] Code blocks maintain proper formatting and syntax highlighting indicators
-- [ ] Lists (ordered and unordered) are correctly converted to markdown syntax
-- [ ] Links and formatting (bold, italic) are preserved in markdown format
-- [ ] Tables are converted to markdown table syntax
-- [ ] Smart paste detection only converts when rich text is detected (plain text pastes normally)
-- [ ] Conversion works across major browsers (Chrome, Firefox, Safari, Edge)
-- [ ] Users can still paste plain text without conversion when needed
-- [ ] All existing paste functionality remains intact for non-rich text content
+- [x] #1 Rich text content pasted into task edit fields is automatically converted to markdown
+- [x] #2 Rich text content pasted into document edit pages is automatically converted to markdown
+- [x] #3 Code blocks maintain proper formatting and syntax highlighting indicators
+- [x] #4 Lists (ordered and unordered) are correctly converted to markdown syntax
+- [x] #5 Links and formatting (bold, italic) are preserved in markdown format
+- [x] #6 Tables are converted to markdown table syntax
+- [x] #7 Smart paste detection only converts when rich text is detected (plain text pastes normally)
+- [x] #8 Conversion works across major browsers (Chrome, Firefox, Safari, Edge)
+- [x] #9 Users can still paste plain text without conversion when needed
+- [x] #10 All existing paste functionality remains intact for non-rich text content
+
+## Implementation Notes
+
+<!-- SECTION:NOTES:BEGIN -->
+
+### Phase 1 — Text, Tables, Lists, Formatting
+
+**Architecture**
+- `PasteAwareMDEditor` — wrapper around `@uiw/react-md-editor` that intercepts `onPaste` on the underlying `<textarea>`.
+- `handlePasteAsMarkdown` — core paste handler: detects rich-text HTML on clipboard, cleans Word garbage, converts to Markdown via Turndown, inserts at caret.
+
+**Key files**
+- `src/web/utils/paste-as-markdown.ts` — conversion engine
+- `src/web/components/PasteAwareMDEditor.tsx` — wrapper component
+- `src/web/components/TaskDetailsModal.tsx` — 4 editors replaced (Description, Plan, Implementation Notes, Final Summary)
+- `src/web/components/DocumentationDetail.tsx` — 1 editor replaced
+
+**Word HTML cleaning (`cleanHtml`)**
+1. Remove noise tags (`<style>`, `<meta>`, `<link>`, `<script>`)
+2. **Convert `mso-list` paragraphs to `<ul>/<li>`** — Word encodes bullet lists as `<p style="mso-list:...">` with conditional-comment wrappers (`<![if !supportLists]>`). Detected *before* inline styles are wiped, grouped into clusters, and replaced with real `<ul>` elements. Word's `mso-list:Ignore` spans are stripped so Turndown can add its own `-` bullets.
+3. Remove all `class` attributes
+4. Convert inline styles to semantic tags (`font-weight:bold` → `<strong>`, `italic` → `<em>`, `underline` → `<u>`, `line-through` → `<s>`) with duplicate-wrap guards
+5. Remove `style` attributes
+6. Remove `<o:p>`, `<img>` (phase 1), empty elements
+7. Flatten lists inside table cells to `<p>` paragraphs (Markdown tables can't nest block elements); unordered lists lose the dash prefix, ordered lists keep `1. ` prefix
+8. Recursively unwrap non-inline elements inside table cells, append `<br>` for paragraph breaks, collapse whitespace, trim trailing `<br>`s
+9. Convert first-row `<td>` to `<th>` so `turndown-plugin-gfm` recognises the table heading
+
+**Turndown configuration**
+- `turndown` + `turndown-plugin-gfm` for GFM tables, strikethrough, task lists
+- Custom rule `keepBr` — forces `<br>` to raw HTML (`<br>`) instead of Turndown's default `  \n` which breaks Markdown table rows
+- Remove `style`, `meta`, `link`, `script`
+
+**Post-processing**
+- Move whitespace inside bold/italic markers to the outside (`**  text **` → ` **text** `)
+- Ensure space after bold/italic closers when they touch plain text (`**text**word` → `**text** word`)
+- Ensure ordered-list markers are followed by a space (`1.item` → `1. item`)
+
+**Smart paste detection**
+- If clipboard has no HTML, fall through to native paste
+- If cleaned HTML converts to Markdown structurally identical to plain text, fall through (avoids converting simple text)
+
+**Dependencies added**
+- `turndown` 7.2.4
+- `turndown-plugin-gfm` 1.0.2
+- `@types/turndown`
+
+### Phase 2 — Images (Done)
+
+**Design: Temp folder + promote on save**
+
+Goal: avoid accumulating orphaned images in `assets/` when users paste images but don't save.
+
+**Paste flow (screenshot tools)**
+1. User pastes screenshot (`image/png` on clipboard, no HTML)
+2. `PasteAwareMDEditor` intercepts, reads `clipboardData.items`
+3. `POST /api/upload?temp=1` — backend saves to `backlog/assets/.temp/{uuid}.png`
+4. Returns `/assets/.temp/{uuid}.png`
+5. Insert Markdown: `![image](/assets/.temp/{uuid}.png)`
+6. Preview works via existing `/assets/*` route
+
+**Paste flow (Word / web pages with `<img>`)**
+1. `handlePasteAsMarkdown` no longer strips `<img>` tags
+2. For each `<img>` in the HTML:
+   - If `src` is a `data:` URI, extract base64 and upload via JSON
+   - If `src` is an HTTP(S) URL, backend downloads and uploads it
+   - If `src` is `file://` or unrecognised, remove the `<img>`
+3. After upload, replace `src` with `/assets/.temp/{uuid}.png`
+4. Turndown emits `![alt](/assets/.temp/{uuid}.png)`
+
+**Save flow (promote)**
+1. User clicks "Save" in task/doc editor
+2. Frontend scans Markdown for `/assets/.temp/` references
+3. `POST /api/assets/promote { urls: ["/assets/.temp/xxx.png", ...] }`
+4. Backend moves each file from `.temp/` to `paste/`
+5. Returns URL mapping: `{ "/assets/.temp/xxx.png": "/assets/paste/xxx.png" }`
+6. Frontend replaces URLs in Markdown, then calls normal save API (`PUT /api/tasks/:id` etc.)
+
+**Why not base64 inline?**
+- Base64 bloats size by ~33%
+- Large screenshots (2~5 MB original → 2.7~6.7 MB base64) cause severe textarea lag in MDEditor
+- Markdown files become unwieldy for version control
+
+**Cleanup**
+- Server startup runs `cleanupTempAssets()` asynchronously (non-blocking)
+- Deletes `.temp/` files older than **30 minutes**
+- Safe: per-file try/catch, never blocks server start
+
+**Backend routes**
+- `POST /api/upload?temp=1` — save file (multipart/form-data or JSON with `url`/`dataUri`), return `/assets/.temp/{filename}`
+- `POST /api/assets/promote` — move `.temp/` → `paste/`, return URL map
+
+**Security considerations for remote URL download**
+- Protocol whitelist: only `http:` and `https:` URLs are accepted; reject `file:`, `ftp:`, `data:`, etc.
+- Host blacklist: block `localhost`, `127.0.0.1`, `::1`, and private IP ranges (`10.x.x.x`, `172.16-31.x.x`, `192.168.x.x`) to mitigate SSRF against local services
+- Redirect limit: cap redirects at 3 hops to prevent redirect chains to internal addresses
+- Content-Type validation: verify the response `Content-Type` starts with `image/` before saving
+- Size limit: abort download if response body exceeds 20 MB to prevent disk exhaustion
+- Timeout: 30s fetch timeout so stalled requests don't hold connections open
+
+**Core API**
+- `src/core/assets.ts` — `AssetManager` class handles all asset operations:
+  - `uploadFile(file, isTemp?)` — multipart upload
+  - `uploadFromDataUri(dataUri, isTemp?)` — base64 decode + upload
+  - `uploadFromUrl(url, isTemp?)` — safe remote download + upload
+  - `promote(urls)` — move `.temp/` → `paste/`
+  - `cleanup(options?)` — delete stale temp files
+  - `downloadImage(url)` — SSRF-safe image fetch (protocol whitelist, private-IP blacklist, redirect limit, content-type & size validation)
+- `ClientError` — thrown for client-input mistakes (invalid data URI, failed download, empty file, etc.); server maps this to HTTP 400
+- `src/core/backlog.ts` — `Core.assets` exposes the manager; server handlers delegate to it
+
+**Frontend changes**
+- `PasteAwareMDEditor`: intercept image paste (screenshot & HTML `<img>`), call upload API
+- `TaskDetailsModal` / `DocumentationDetail`: pre-save promote step before `PUT`
+- `paste-as-markdown.ts`: async `handlePasteAsMarkdown` with optional `ImageUploader` callback
+
+### Bugfixes (2026-05-09)
+
+**Excel table paste not converted to Markdown**
+- Root cause: Excel wraps tables in `<colgroup><col>...</colgroup>`. Turndown GFM table rule does not recognise tables that contain `<colgroup>`, so the raw HTML was preserved instead of being converted to `| col1 | col2 |`.
+- Fix: `cleanHtml` now strips `<colgroup>` and `<col>` tags before conversion.
+- File: `src/web/utils/paste-as-markdown.ts`
+
+**Excel paste loses screenshot image**
+- Root cause: Excel puts the selected range on the clipboard as both `text/html` (table) and `image/png` (screenshot). The previous code only handled one or the other; when HTML was present the standalone image blob was ignored.
+- Fix: `handlePasteAsMarkdown` now returns the Markdown `string | null` instead of `boolean`. `PasteAwareMDEditor` receives the markdown, appends any standalone image blob (`\n\n![image](url)`), and inserts both at the caret in one shot.
+- Files: `src/web/utils/paste-as-markdown.ts`, `src/web/components/PasteAwareMDEditor.tsx`
+
+**Word `file://` image references**
+- Investigated but reverted. Word copies images as `file:///C:/Users/...` local paths. Browser cannot read them, and backend `file://` access was rejected for security reasons. Current behaviour: `file://` `<img>` tags are silently removed. Users can paste screenshots directly (Win+Shift+S) which work as `image/png` blobs.
+
+<!-- SECTION:NOTES:END -->
diff --git a/backlog/tasks/back-467 - Add-local-file-preview-with-syntax-highlighting-and-line-numbers.md b/backlog/tasks/back-467 - Add-local-file-preview-with-syntax-highlighting-and-line-numbers.md
new file mode 100644
index 000000000..9b58caa40
--- /dev/null
+++ b/backlog/tasks/back-467 - Add-local-file-preview-with-syntax-highlighting-and-line-numbers.md	
@@ -0,0 +1,88 @@
+---
+id: BACK-467
+title: Add local file preview with syntax highlighting and line numbers
+status: Done
+assignee: kuwork
+created_date: '2026-04-26'
+updated_date: '2026-05-07 09:25'
+labels:
+  - enhancement
+  - web-ui
+dependencies: []
+references:
+  - src/server/index.ts
+  - src/web/components/FilePreviewModal.tsx
+  - src/web/components/MermaidMarkdown.tsx
+  - src/web/components/TaskDetailsModal.tsx:707-715
+  - src/web/lib/api.ts
+  - src/web/styles/style.css
+  
+priority: medium
+---
+
+## Description
+
+Add a local file preview feature to the Web UI that allows users to click on local file paths in task References, Documentation, and Markdown content (Description, Plan, Notes, Final Summary) to view file contents directly in a modal.
+
+**Path semantics:** Paths are always resolved relative to the project root (the directory containing `backlog/`). Users should write paths as relative paths from the project root — for example, `src/server/index.ts` or `CLI-INSTRUCTIONS.md`. Absolute paths are not supported, and attempts to traverse above the project root (`../`) are rejected by the API for security.
+
+The preview supports:
+- Full file viewing for code and markdown files
+- Syntax highlighting via MDEditor.Markdown with Prism
+- Line numbers rendered via CSS counters
+- Partial line ranges (e.g., `src/server/index.ts:35-39`) with correct offset numbering
+- Language detection from file extension for syntax highlighting
+- Fallback to normal link behavior when a file does not exist
+
+## Acceptance Criteria
+<!-- AC:BEGIN -->
+- [x] #1 Backend /api/file-content endpoint reads local files within project root
+- [x] #2 API supports optional line ranges (e.g., file.ts:35-39) with security checks
+- [x] #3 API prevents directory traversal outside project root
+- [x] #4 FilePreviewModal component renders code files with syntax highlighting
+- [x] #5 FilePreviewModal displays line numbers using CSS counters
+- [x] #6 Partial line ranges show correct starting line numbers
+- [x] #7 MermaidMarkdown intercepts local file links to open preview modal
+- [x] #8 References and Documentation local paths are clickable in TaskDetailsModal
+- [x] #9 Non-existent files fall back to normal browser link behavior
+<!-- AC:END -->
+
+## Definition of Done
+
+- [x] All acceptance criteria implemented and verified
+- [x] Code reviewed and feedback addressed
+- [x] No unrelated changes to existing markdown/link behavior
+- [x] Backlog task metadata accurate (correct task ID, assignee, and AC)
+
+## Implementation Plan
+
+<!-- SECTION:PLAN:BEGIN -->
+## Implementation Plan
+
+### Backend
+1. Add `/api/file-content` route to `src/server/index.ts`
+2. Parse optional line range from path parameter (`file:lineStart-lineEnd`)
+3. Resolve path within project root and reject directory traversal
+4. Return file content, path, line range, total lines, and markdown flag
+
+### Frontend API
+1. Add `fetchFileContent(path)` to `src/web/lib/api.ts`
+
+### File Preview Modal
+1. Create `src/web/components/FilePreviewModal.tsx`
+2. Detect language from file extension for fenced code blocks
+3. Render markdown files with `MermaidMarkdown`
+4. Render code files via `MDEditor.Markdown` wrapped in fenced blocks
+5. Add CSS counter-based line numbers with `counterReset` for partial ranges
+
+### Markdown Link Interception
+1. Add `onFileClick` prop to `MermaidMarkdown`
+2. Custom `a` component for `MDEditor.Markdown`
+3. `isExternalLink()` to distinguish URLs from local paths
+4. Async click handler: verify file exists via API, then preview or fallback
+
+### Task Details Modal
+1. Pass `onFileClick` to all `MermaidMarkdown` instances (Description, Plan, Notes, Final Summary)
+2. Render local file paths in References and Documentation as clickable buttons
+3. Open `FilePreviewModal` on click
+<!-- SECTION:PLAN:END -->
diff --git a/backlog/tasks/back-475 - Add-Word-(docx)-upload-to-enable-image-extraction-for-pasted-Word-content.md b/backlog/tasks/back-475 - Add-Word-(docx)-upload-to-enable-image-extraction-for-pasted-Word-content.md
new file mode 100644
index 000000000..8453bab16
--- /dev/null
+++ b/backlog/tasks/back-475 - Add-Word-(docx)-upload-to-enable-image-extraction-for-pasted-Word-content.md	
@@ -0,0 +1,111 @@
+---
+id: BACK-475
+title: Add Word (.docx) upload to enable image extraction for pasted Word content
+status: Done
+assignee: []
+created_date: '2026-05-11 20:05'
+labels:
+  - web-ui
+  - enhancement
+  - markdown
+  - editor
+dependencies: []
+priority: medium
+ordinal: 24000
+---
+
+## Description
+
+Allow the Web UI rich-text editor to directly upload Word documents (`.docx`), automatically convert their content to Markdown format, and import it into the editor. If the Word document contains images, they should be extracted and uploaded to the temporary file directory, with corresponding image references inserted into the Markdown.
+
+### Background
+
+The existing editor already supports pasting rich text and automatically converting it to Markdown (BACK-208), but users still need a way to directly upload `.docx` files. This feature should reuse the existing image upload and temporary file management mechanisms (`backlog/assets/.temp/` and the promote flow) to maintain architectural consistency.
+
+### Expected Behavior
+
+1. Add an "Upload Word Document" entry to the editor toolbar or drag-and-drop area.
+2. After the user selects a `.docx` file, the frontend sends it to the backend for parsing.
+3. The backend extracts the text content from the document and converts it to Markdown format.
+4. The backend extracts embedded images from the document, saves them to the `backlog/assets/.temp/` directory, and returns temporary URLs.
+5. The frontend inserts the Markdown content and image references into the editor.
+6. When the user saves, the existing `promote` flow migrates images from `.temp/` to the permanent directory.
+
+## Acceptance Criteria
+
+- [x] #1 Support uploading `.docx` files via file picker or drag-and-drop.
+- [x] #2 Word document text content (paragraphs, headings, lists, tables, bold/italic/underline, etc.) is correctly converted to Markdown.
+- [x] #3 Embedded images in Word documents are extracted and uploaded to `backlog/assets/.temp/`, generating temporary URLs.
+- [x] #4 Images in the converted Markdown are inserted at the correct position in the form `![alt](/assets/.temp/{uuid}.png)`.
+- [x] #5 Large files (>20MB) or malformed documents give clear error messages.
+- [x] #6 New dedicated API `POST /api/docx/convert` handles `.docx` parsing.
+- [x] #7 When the user clicks save, temporary images go through the existing `POST /api/assets/promote` flow to be promoted.
+- [x] #8 Does not break the existing paste-as-Markdown functionality (BACK-208).
+
+## Implementation Notes
+
+<!-- SECTION:NOTES:BEGIN -->
+
+### Technical Approach Reference
+
+**Backend Parsing**
+- Optional libraries: `mammoth` (convert `.docx` to HTML, then reuse existing Turndown logic) or `docx-to-markdown` class libraries.
+- Recommended: `mammoth` first converts `.docx` → HTML, then reuses the `cleanHtml` + Turndown chain from `src/web/utils/paste-as-markdown.ts` to ensure consistency with paste behavior.
+- `mammoth` supports image conversion callbacks: embedded images can be exported as buffers, then reused with `AssetManager.uploadFromDataUri` or `uploadFile` to write to `.temp/`.
+
+**Frontend Interaction**
+- Add an "Upload Word" button / drag-and-drop area in `PasteAwareMDEditor` or the editor toolbar.
+- Show progress or loading state during upload.
+- After parsing is complete, insert Markdown into the editor's current cursor position in one go (or replace current content; interaction to be confirmed).
+
+**API Design**
+```
+POST /api/docx/convert
+Content-Type: multipart/form-data
+
+file: <.docx file>
+
+Response:
+{
+  "markdown": "# Title\n\nParagraph...",
+  "images": [
+    { "tempUrl": "/assets/.temp/uuid1.png", "alt": "image1" }
+  ]
+}
+```
+
+**Image Handling**
+- Reuse `AssetManager` from `src/core/assets.ts`.
+- Each extracted image is saved via `uploadFile(buffer, { isTemp: true })`.
+- The returned `tempUrl` is embedded in Markdown, and subsequent promote logic is identical to BACK-208.
+
+**Error Handling**
+- Non-`.docx` extension → 400.
+- Parsing failure / corrupted file → 400 with readable error message.
+- Single image exceeds size limit → skip the image and warn in the response, or fail entirely (strategy to be determined).
+
+### Post-Completion Fixes (2026-05-11)
+
+**Table normalization in docx upload**
+- Problem: Uploading `.docx` files with complex tables (nested paragraphs, lists, bold text inside cells) produced raw `<table>` HTML instead of GFM Markdown tables.
+- Root cause: Backend `docx-converter.ts` sent mammoth HTML directly to Turndown without the `cleanHtml` preprocessing that the paste path already had.
+- Fix: Backend now returns raw HTML (`{ html, images, messages }`); frontend `PasteAwareMDEditor.handleDocxUpload` calls `cleanHtml` + Turndown in the browser, reusing the exact same pipeline as paste-as-markdown. This ensures tables are flattened (block elements unwrapped, lists prefixed, first row promoted to `<th>`) before conversion.
+
+**Image preservation in docx upload**
+- Problem: `cleanHtml` removed empty `<p>/<span>/<div>` elements. A `<p>` containing only an `<img>` has no `textContent`, so it was stripped and images disappeared from the output.
+- Fix: `cleanHtml` gained a `keepMedia` option. `handleDocxUpload` passes `{ keepMedia: true }` so server-side extracted images (already uploaded to `.temp/`) are preserved. The paste path keeps the default behaviour (invalid local images are still filtered out by the existing upload/replace logic in `handlePasteAsMarkdown`).
+
+**HTML cleanup unified on the frontend**
+- Problem: The backend `docx-converter.ts` performed Turndown conversion directly on mammoth HTML, while the frontend paste path ran `cleanHtml` first. This caused divergent output — complex tables worked for paste but not for file upload.
+- Fix: `docx-converter.ts` now returns raw mammoth HTML (`{ html, images, messages }`). The frontend (`PasteAwareMDEditor.handleDocxUpload`) calls `cleanHtml` + Turndown in the browser, using the exact same pipeline as `handlePasteAsMarkdown`. This guarantees paste and upload produce identical Markdown.
+
+<!-- SECTION:NOTES:END -->
+
+## Definition of Done
+
+<!-- DOD:BEGIN -->
+- [x] #1 `bunx tsc --noEmit` passes when TypeScript touched.
+- [x] #2 `bun run check .` passes when formatting/linting touched.
+- [x] #3 `bun test` (or scoped test) passes.
+- [x] #4 Manual test: upload a Word document with images, confirm Markdown rendering and image promote work correctly.
+<!-- DOD:END -->
diff --git a/backlog/tasks/back-476 - Fix-inline-code-HTML-escaping-in-markdown-renderer.md b/backlog/tasks/back-476 - Fix-inline-code-HTML-escaping-in-markdown-renderer.md
new file mode 100644
index 000000000..76aa73cd5
--- /dev/null
+++ b/backlog/tasks/back-476 - Fix-inline-code-HTML-escaping-in-markdown-renderer.md	
@@ -0,0 +1,79 @@
+---
+id: BACK-476
+title: Fix HTML-entity escaping inside inline code in markdown renderer
+status: Done
+assignee: []
+created_date: '2026-05-13 23:08'
+labels:
+  - web-ui
+  - bug
+  - wiki
+  - markdown
+dependencies: []
+priority: medium
+ordinal: 24001
+---
+
+# back-476 - Fix HTML-entity escaping inside inline code in markdown renderer
+
+## Description
+
+The `sanitizeMarkdownSource` helper in `MermaidMarkdown.tsx` escapes `<` to `&lt;` to prevent raw HTML-like tags from being parsed by the Markdown renderer. However, it was applying this escape indiscriminately, including inside inline code blocks (e.g. `` `<id>` ``) and fenced code blocks.
+
+Because Markdown renderers already preserve code content verbatim, this caused double encoding: the user saw `&lt;id&gt;` instead of `<id>`.
+
+This component is used across multiple views — wiki pages, task details (description, plan, notes, final summary), documentation, decisions, and file previews — so the bug affected all of them.
+
+## Root Cause
+
+- `source.replace(/<(?=[A-Za-z])/g, ...)` runs over the entire markdown source without excluding code regions.
+- Inline code like `` `backlog task <id>` `` becomes `` `backlog task &lt;id>` `` after sanitization.
+- The Markdown renderer then outputs `<code>backlog task &lt;id></code>`, and the browser displays the literal `&lt;` entity.
+
+## Fix
+
+Updated `sanitizeMarkdownSource` to first collect protected ranges for:
+
+- Fenced code blocks (```...```)
+- Inline code (`...`)
+
+The `<` replacement is now skipped when the match offset falls inside any protected range.
+
+## Implementation Plan
+
+1. Identify all fenced code blocks and inline code spans in the raw markdown source before running the `<` escape replacement.
+2. Record the start/end offsets of each protected range.
+3. During the existing `replace` pass, check whether the current match offset lies inside any protected range.
+4. If inside a code region, return the original `<` unchanged; otherwise apply the existing logic (escape to `&lt;` unless it is a URI/email autolink).
+
+## Implementation Notes
+
+<!-- SECTION:NOTES:BEGIN -->
+
+**File:** `src/web/components/MermaidMarkdown.tsx`
+
+Added two regex passes before the existing `<` replacement to mark code regions as protected:
+
+1. **Fenced code blocks:** `/```[\s\S]*?```/g`
+2. **Inline code:** ``/`[^`\n]+`/g``
+
+During the replacement loop, each match offset is checked against the collected protected ranges. If the offset falls inside a code block or inline code segment, the original `<` is preserved instead of being escaped to `&lt;`.
+
+The existing URI/email autolink exemptions (`<mailto:...>`, `<user@example.com>`) continue to work for matches outside code regions.
+
+<!-- SECTION:NOTES:END -->
+
+## Acceptance Criteria
+
+- [x] Inline code containing `<` renders correctly (e.g. `` `<id>` `` displays as `<id>`, not `&lt;id&gt;`)
+- [x] Fenced code blocks containing `<` render correctly
+- [x] Regular text outside code still has `<Something>` escaped to prevent accidental HTML tag parsing
+- [x] URI autolinks (e.g. `<mailto:...>`) and email autolinks remain unaffected
+
+## Definition of Done
+
+<!-- DOD:BEGIN -->
+- [x] #1 `bunx tsc --noEmit` passes.
+- [x] #2 Type-check confirms no new errors in `src/web/components/MermaidMarkdown.tsx`.
+- [x] #3 Manual test: inline code like `` `<id>` `` displays `<id>` instead of `&lt;id&gt;` across wiki, task details, documentation, and decision views.
+<!-- DOD:END -->
diff --git a/bun.lock b/bun.lock
index 06438b333..bf08b00ce 100644
--- a/bun.lock
+++ b/bun.lock
@@ -24,6 +24,7 @@
         "install": "0.13.0",
         "jsdom": "29.0.2",
         "lint-staged": "16.4.0",
+        "mammoth": "1.12.0",
         "mermaid": "11.14.0",
         "neo-neo-bblessed": "1.0.9",
         "picocolors": "1.1.1",
@@ -33,6 +34,8 @@
         "react-router-dom": "7.14.1",
         "react-tooltip": "5.30.1",
         "tailwindcss": "4.2.2",
+        "turndown": "7.2.4",
+        "turndown-plugin-gfm": "1.0.2",
       },
       "optionalDependencies": {
         "backlog.md-darwin-arm64": "*",
@@ -191,6 +194,8 @@
 
     "@mermaid-js/parser": ["@mermaid-js/parser@1.1.0", "", { "dependencies": { "langium": "^4.0.0" } }, "sha512-gxK9ZX2+Fex5zu8LhRQoMeMPEHbc73UKZ0FQ54YrQtUxE1VVhMwzeNtKRPAu5aXks4FasbMe4xB4bWrmq6Jlxw=="],
 
+    "@mixmark-io/domino": ["@mixmark-io/domino@2.2.0", "", {}, "sha512-Y28PR25bHXUg88kCV7nivXrP2Nj2RueZ3/l/jdx6J9f8J4nsEGcgX0Qe6lt7Pa+J79+kPiJU3LguR6O/6zrLOw=="],
+
     "@modelcontextprotocol/sdk": ["@modelcontextprotocol/sdk@1.29.0", "", { "dependencies": { "@hono/node-server": "^1.19.9", "ajv": "^8.17.1", "ajv-formats": "^3.0.1", "content-type": "^1.0.5", "cors": "^2.8.5", "cross-spawn": "^7.0.5", "eventsource": "^3.0.2", "eventsource-parser": "^3.0.0", "express": "^5.2.1", "express-rate-limit": "^8.2.1", "hono": "^4.11.4", "jose": "^6.1.3", "json-schema-typed": "^8.0.2", "pkce-challenge": "^5.0.0", "raw-body": "^3.0.0", "zod": "^3.25 || ^4.0", "zod-to-json-schema": "^3.25.1" }, "peerDependencies": { "@cfworker/json-schema": "^4.1.1" }, "optionalPeers": ["@cfworker/json-schema"] }, "sha512-zo37mZA9hJWpULgkRpowewez1y6ML5GsXJPY8FI0tBBCd77HEvza4jDqRKOXgHNn867PVGCyTdzqpz0izu5ZjQ=="],
 
     "@parcel/watcher": ["@parcel/watcher@2.5.1", "", { "dependencies": { "detect-libc": "^1.0.3", "is-glob": "^4.0.3", "micromatch": "^4.0.5", "node-addon-api": "^7.0.0" }, "optionalDependencies": { "@parcel/watcher-android-arm64": "2.5.1", "@parcel/watcher-darwin-arm64": "2.5.1", "@parcel/watcher-darwin-x64": "2.5.1", "@parcel/watcher-freebsd-x64": "2.5.1", "@parcel/watcher-linux-arm-glibc": "2.5.1", "@parcel/watcher-linux-arm-musl": "2.5.1", "@parcel/watcher-linux-arm64-glibc": "2.5.1", "@parcel/watcher-linux-arm64-musl": "2.5.1", "@parcel/watcher-linux-x64-glibc": "2.5.1", "@parcel/watcher-linux-x64-musl": "2.5.1", "@parcel/watcher-win32-arm64": "2.5.1", "@parcel/watcher-win32-ia32": "2.5.1", "@parcel/watcher-win32-x64": "2.5.1" } }, "sha512-dfUnCxiN9H4ap84DvD2ubjw+3vUNpstxa0TneY/Paat8a3R4uQZDLSvWjmznAY/DoahqTHl9V46HF/Zs3F29pg=="],
@@ -363,6 +368,8 @@
 
     "@upsetjs/venn.js": ["@upsetjs/venn.js@2.0.0", "", { "optionalDependencies": { "d3-selection": "^3.0.0", "d3-transition": "^3.0.1" } }, "sha512-WbBhLrooyePuQ1VZxrJjtLvTc4NVfpOyKx0sKqioq9bX1C1m7Jgykkn8gLrtwumBioXIqam8DLxp88Adbue6Hw=="],
 
+    "@xmldom/xmldom": ["@xmldom/xmldom@0.8.13", "", {}, "sha512-KRYzxepc14G/CEpEGc3Yn+JKaAeT63smlDr+vjB8jRfgTBBI9wRj/nkQEO+ucV8p8I9bfKLWp37uHgFrbntPvw=="],
+
     "@xterm/headless": ["@xterm/headless@5.5.0", "", {}, "sha512-5xXB7kdQlFBP82ViMJTwwEc3gKCLGKR/eoxQm4zge7GPBl86tCdI0IdPJjoKd8mUSFXz5V7i/25sfsEkP4j46g=="],
 
     "abort-controller": ["abort-controller@3.0.0", "", { "dependencies": { "event-target-shim": "^5.0.0" } }, "sha512-h8lQ8tacZYnR3vNQTgibj+tODHI5/+l06Au2Pcriv/Gmet0eaj4TwWH41sO9wnHDiQsEj19q0drzdWdeAHtweg=="],
@@ -405,6 +412,8 @@
 
     "bidi-js": ["bidi-js@1.0.3", "", { "dependencies": { "require-from-string": "^2.0.2" } }, "sha512-RKshQI1R3YQ+n9YJz2QQ147P66ELpa1FQEg20Dk8oW9t2KgLbpDLLp9aGZ7y8WHSshDknG0bknqGw5/tyCs5tw=="],
 
+    "bluebird": ["bluebird@3.4.7", "", {}, "sha512-iD3898SR7sWVRHbiQv+sHUtHnMvC1o3nW5rAcqnq3uOn07DSAppZYUkIGslDz6gXC7HfunPe7YVBgoEJASPcHA=="],
+
     "bmp-ts": ["bmp-ts@1.0.9", "", {}, "sha512-cTEHk2jLrPyi+12M3dhpEbnnPOsaZuq7C45ylbbQIiWgDFZq4UVYPEY5mlqjvsj/6gJv9qX5sa+ebDzLXT28Vw=="],
 
     "body-parser": ["body-parser@2.2.2", "", { "dependencies": { "bytes": "^3.1.2", "content-type": "^1.0.5", "debug": "^4.4.3", "http-errors": "^2.0.0", "iconv-lite": "^0.7.0", "on-finished": "^2.4.1", "qs": "^6.14.1", "raw-body": "^3.0.1", "type-is": "^2.0.1" } }, "sha512-oP5VkATKlNwcgvxi0vM0p/D3n2C3EReYVX+DNYs5TjZFn/oQt2j+4sVJtSMr18pdRr8wjTcBl6LoV+FUwzPmNA=="],
@@ -459,6 +468,8 @@
 
     "cookie-signature": ["cookie-signature@1.2.2", "", {}, "sha512-D76uU73ulSXrD1UXF4KE2TMxVVwhsnCgfAyTg9k8P6KGZjlXKrOLe4dJQKI3Bxi5wjesZoFXJWElNWBjPZMbhg=="],
 
+    "core-util-is": ["core-util-is@1.0.3", "", {}, "sha512-ZQBvi1DcpJ4GDqanjucZ2Hj3wEO5pZDS89BWbkcrvdxksJorwUDDZamX9ldFkp9aw2lmBDLgkObEA4DWNJ9FYQ=="],
+
     "cors": ["cors@2.8.5", "", { "dependencies": { "object-assign": "^4", "vary": "^1" } }, "sha512-KIHbLJqu73RGr/hnbrO9uBeixNGuvSQjul/jdFvS/KFSIH1hWVd1ng7zOHx+YrEfInLG7q4n6GHQ9cDtxv/P6g=="],
 
     "cose-base": ["cose-base@1.0.3", "", { "dependencies": { "layout-base": "^1.0.0" } }, "sha512-s9whTXInMSgAp/NVXVNuVxVKzGH2qck3aQlVHxDCdAEPgtMKwc4Wq6/QKhgdEdgbLSi9rBTAcPoRa6JpiG4ksg=="],
@@ -565,10 +576,14 @@
 
     "devlop": ["devlop@1.1.0", "", { "dependencies": { "dequal": "^2.0.0" } }, "sha512-RWmIqhcFf1lRYBvNmr7qTNuyCt/7/ns2jbpp1+PalgE/rDQcBT0fioSMUpJ93irlUhC5hrg4cYqe6U+0ImW0rA=="],
 
+    "dingbat-to-unicode": ["dingbat-to-unicode@1.0.1", "", {}, "sha512-98l0sW87ZT58pU4i61wa2OHwxbiYSbuxsCBozaVnYX2iCnr3bLM3fIes1/ej7h1YdOKuKt/MLs706TVnALA65w=="],
+
     "direction": ["direction@2.0.1", "", { "bin": { "direction": "cli.js" } }, "sha512-9S6m9Sukh1cZNknO1CWAr2QAWsbKLafQiyM5gZ7VgXHeuaoUwffKN4q6NC4A/Mf9iiPlOXQEKW/Mv/mh9/3YFA=="],
 
     "dompurify": ["dompurify@3.4.0", "", { "optionalDependencies": { "@types/trusted-types": "^2.0.7" } }, "sha512-nolgK9JcaUXMSmW+j1yaSvaEaoXYHwWyGJlkoCTghc97KgGDDSnpoU/PlEnw63Ah+TGKFOyY+X5LnxaWbCSfXg=="],
 
+    "duck": ["duck@0.1.12", "", { "dependencies": { "underscore": "^1.13.1" } }, "sha512-wkctla1O6VfP89gQ+J/yDesM0S7B7XLXjKGzXxMDVFg7uEn706niAtyYovKbyq1oT9YwDcly721/iUWoc8MVRg=="],
+
     "dunder-proto": ["dunder-proto@1.0.1", "", { "dependencies": { "call-bind-apply-helpers": "^1.0.1", "es-errors": "^1.3.0", "gopd": "^1.2.0" } }, "sha512-KIN/nDJBQRcXw0MLVhZE9iQHmG68qAVIBg9CqmUYjmQIhgij9U5MFvrqkUL5FbtyyzZuOeOt0zdeRe4UY7ct+A=="],
 
     "eastasianwidth": ["eastasianwidth@0.3.0", "", {}, "sha512-JqasYqGO32J2c91uYKdhu1vNmXGADaLB7OOgjAhjMvpjdvGb0tsYcuwn381MwqCg4YBQDtByQcNlFYuv2kmOug=="],
@@ -717,6 +732,8 @@
 
     "image-q": ["image-q@4.0.0", "", { "dependencies": { "@types/node": "16.9.1" } }, "sha512-PfJGVgIfKQJuq3s0tTDOKtztksibuUEbJQIYT3by6wctQo+Rdlh7ef4evJ5NCdxY4CfMbvFkocEwbl4BF8RlJw=="],
 
+    "immediate": ["immediate@3.0.6", "", {}, "sha512-XXOFtyqDjNDAQxVfYxuF7g9Il/IbWmmlQg2MYKOH8ExIT1qg6xc4zyS3HaEEATgs1btfzxq15ciUiY7gjSXRGQ=="],
+
     "inherits": ["inherits@2.0.4", "", {}, "sha512-k/vGaX4/Yla3WzyMCvTQOXYeIHvqOKtnqBduzTHpzpQZzAskKMhZ2K+EnBiSM9zGSoIFeMpXKxa4dYeZIQqewQ=="],
 
     "inline-style-parser": ["inline-style-parser@0.2.4", "", {}, "sha512-0aO8FkhNZlj/ZIbNi7Lxxr12obT7cL1moPfE4tg1LkX7LlLfC6DeX4l2ZEud1ukP9jNQyNnfzQVqwbwmAATY4Q=="],
@@ -753,6 +770,8 @@
 
     "is-promise": ["is-promise@4.0.0", "", {}, "sha512-hvpoI6korhJMnej285dSg6nu1+e6uxs7zG3BYAm5byqDsgJNWwxzM6z6iZiAgQR4TJ30JmBTOwqZUw3WlyH3AQ=="],
 
+    "isarray": ["isarray@1.0.0", "", {}, "sha512-VLghIWNM6ELQzo7zwmcg0NmTVyWKYjvIeM83yjp0wRDTmUnrM678fQbcKBo6n2CJEF0szoG//ytg+TKla89ALQ=="],
+
     "isexe": ["isexe@2.0.0", "", {}, "sha512-RHxMLp9lnKHGHRng9QFhRCMbYAcVpn69smSGcq3f36xjgVVWThj4qqLbTLlq7Ssj8B+fIQ1EuCEGI2lKsyQeIw=="],
 
     "jimp": ["jimp@1.6.0", "", { "dependencies": { "@jimp/core": "1.6.0", "@jimp/diff": "1.6.0", "@jimp/js-bmp": "1.6.0", "@jimp/js-gif": "1.6.0", "@jimp/js-jpeg": "1.6.0", "@jimp/js-png": "1.6.0", "@jimp/js-tiff": "1.6.0", "@jimp/plugin-blit": "1.6.0", "@jimp/plugin-blur": "1.6.0", "@jimp/plugin-circle": "1.6.0", "@jimp/plugin-color": "1.6.0", "@jimp/plugin-contain": "1.6.0", "@jimp/plugin-cover": "1.6.0", "@jimp/plugin-crop": "1.6.0", "@jimp/plugin-displace": "1.6.0", "@jimp/plugin-dither": "1.6.0", "@jimp/plugin-fisheye": "1.6.0", "@jimp/plugin-flip": "1.6.0", "@jimp/plugin-hash": "1.6.0", "@jimp/plugin-mask": "1.6.0", "@jimp/plugin-print": "1.6.0", "@jimp/plugin-quantize": "1.6.0", "@jimp/plugin-resize": "1.6.0", "@jimp/plugin-rotate": "1.6.0", "@jimp/plugin-threshold": "1.6.0", "@jimp/types": "1.6.0", "@jimp/utils": "1.6.0" } }, "sha512-YcwCHw1kiqEeI5xRpDlPPBGL2EOpBKLwO4yIBJcXWHPj5PnA5urGq0jbyhM5KoNpypQ6VboSoxc9D8HyfvngSg=="],
@@ -771,6 +790,8 @@
 
     "json-schema-typed": ["json-schema-typed@8.0.2", "", {}, "sha512-fQhoXdcvc3V28x7C7BMs4P5+kNlgUURe2jmUT1T//oBRMDrqy1QPelJimwZGo7Hg9VPV3EQV5Bnq4hbFy2vetA=="],
 
+    "jszip": ["jszip@3.10.1", "", { "dependencies": { "lie": "~3.3.0", "pako": "~1.0.2", "readable-stream": "~2.3.6", "setimmediate": "^1.0.5" } }, "sha512-xXDvecyTpGLrqFrvkrUSoxxfJI5AH7U8zxxtVclpsUtMCq4JQ290LY8AW5c7Ggnr/Y/oK+bQMbqK2qmtk3pN4g=="],
+
     "katex": ["katex@0.16.25", "", { "dependencies": { "commander": "^8.3.0" }, "bin": { "katex": "cli.js" } }, "sha512-woHRUZ/iF23GBP1dkDQMh1QBad9dmr8/PAwNA54VrSOVYgI12MAcE14TqnDdQOdzyEonGzMepYnqBMYdsoAr8Q=="],
 
     "khroma": ["khroma@2.1.0", "", {}, "sha512-Ls993zuzfayK269Svk9hzpeGUKob/sIgZzyHYdjQoAdQetRKpOLj+k/QQQ/6Qi0Yz65mlROrfd+Ev+1+7dz9Kw=="],
@@ -783,6 +804,8 @@
 
     "layout-base": ["layout-base@1.0.2", "", {}, "sha512-8h2oVEZNktL4BH2JCOI90iD1yXwL6iNW7KcCKT2QZgQJR2vbqDsldCTPRU9NifTCqHZci57XvQQ15YTu+sTYPg=="],
 
+    "lie": ["lie@3.3.0", "", { "dependencies": { "immediate": "~3.0.5" } }, "sha512-UaiMJzeWRlEujzAuw5LokY1L5ecNQYZKfmyZ9L7wDHb/p5etKaxXhohBcrw0EYby+G/NA52vRSN4N39dxHAIwQ=="],
+
     "lightningcss": ["lightningcss@1.32.0", "", { "dependencies": { "detect-libc": "^2.0.3" }, "optionalDependencies": { "lightningcss-android-arm64": "1.32.0", "lightningcss-darwin-arm64": "1.32.0", "lightningcss-darwin-x64": "1.32.0", "lightningcss-freebsd-x64": "1.32.0", "lightningcss-linux-arm-gnueabihf": "1.32.0", "lightningcss-linux-arm64-gnu": "1.32.0", "lightningcss-linux-arm64-musl": "1.32.0", "lightningcss-linux-x64-gnu": "1.32.0", "lightningcss-linux-x64-musl": "1.32.0", "lightningcss-win32-arm64-msvc": "1.32.0", "lightningcss-win32-x64-msvc": "1.32.0" } }, "sha512-NXYBzinNrblfraPGyrbPoD19C1h9lfI/1mzgWYvXUTe414Gz/X1FD2XBZSZM7rRTrMA8JL3OtAaGifrIKhQ5yQ=="],
 
     "lightningcss-android-arm64": ["lightningcss-android-arm64@1.32.0", "", { "os": "android", "cpu": "arm64" }, "sha512-YK7/ClTt4kAK0vo6w3X+Pnm0D2cf2vPHbhOXdoNti1Ga0al1P4TBZhwjATvjNwLEBCnKvjJc2jQgHXH0NEwlAg=="],
@@ -819,10 +842,14 @@
 
     "longest-streak": ["longest-streak@3.1.0", "", {}, "sha512-9Ri+o0JYgehTaVBBDoMqIl8GXtbWg711O3srftcHhZ0dqnETqLaoIK0x17fUw9rFSlK/0NlsKe0Ahhyl5pXE2g=="],
 
+    "lop": ["lop@0.4.2", "", { "dependencies": { "duck": "^0.1.12", "option": "~0.2.1", "underscore": "^1.13.1" } }, "sha512-RefILVDQ4DKoRZsJ4Pj22TxE3omDO47yFpkIBoDKzkqPRISs5U1cnAdg/5583YPkWPaLIYHOKRMQSvjFsO26cw=="],
+
     "lru-cache": ["lru-cache@11.3.5", "", {}, "sha512-NxVFwLAnrd9i7KUBxC4DrUhmgjzOs+1Qm50D3oF1/oL+r1NpZ4gA7xvG0/zJ8evR7zIKn4vLf7qTNduWFtCrRw=="],
 
     "magic-string": ["magic-string@0.30.21", "", { "dependencies": { "@jridgewell/sourcemap-codec": "^1.5.5" } }, "sha512-vd2F4YUyEXKGcLHoq+TEyCjxueSeHnFxyyjNp80yg0XV4vUhnDer/lvvlqM/arB5bXQN5K2/3oinyCRyx8T2CQ=="],
 
+    "mammoth": ["mammoth@1.12.0", "", { "dependencies": { "@xmldom/xmldom": "^0.8.6", "argparse": "~1.0.3", "base64-js": "^1.5.1", "bluebird": "~3.4.0", "dingbat-to-unicode": "^1.0.1", "jszip": "^3.7.1", "lop": "^0.4.2", "path-is-absolute": "^1.0.0", "underscore": "^1.13.1", "xmlbuilder": "^10.0.0" }, "bin": { "mammoth": "bin/mammoth" } }, "sha512-cwnK1RIcRdDMi2HRx2EXGYlxqIEh0Oo3bLhorgnsVJi2UkbX1+jKxuBNR9PC5+JaX7EkmJxFPmo6mjLpqShI2w=="],
+
     "markdown-table": ["markdown-table@3.0.4", "", {}, "sha512-wiYz4+JrLyb/DqW2hkFJxP7Vd7JuTDm77fvbM8VfEQdmSMqcImWeeRbHwZjBjIFki/VaMK2BhFi7oUUZeM5bqw=="],
 
     "marked": ["marked@16.4.2", "", { "bin": { "marked": "bin/marked.js" } }, "sha512-TI3V8YYWvkVf3KJe1dRkpnjs68JUPyEa5vjKrp1XEEJUAOaQc+Qj+L1qWbPd0SJuAdQkFU0h73sXXqwDYxsiDA=="],
@@ -959,9 +986,11 @@
 
     "onetime": ["onetime@7.0.0", "", { "dependencies": { "mimic-function": "^5.0.0" } }, "sha512-VXJjc87FScF88uafS3JllDgvAm+c/Slfz06lorj2uAY34rlUu0Nt+v8wreiImcrgAjjIHp1rXpTDlLOGw29WwQ=="],
 
+    "option": ["option@0.2.4", "", {}, "sha512-pkEqbDyl8ou5cpq+VsnQbe/WlEy5qS7xPzMS1U55OCG9KPvwFD46zDbxQIj3egJSFc3D+XhYOPUzz49zQAVy7A=="],
+
     "package-manager-detector": ["package-manager-detector@1.5.0", "", {}, "sha512-uBj69dVlYe/+wxj8JOpr97XfsxH/eumMt6HqjNTmJDf/6NO9s+0uxeOneIz3AsPt2m6y9PqzDzd3ATcU17MNfw=="],
 
-    "pako": ["pako@0.2.9", "", {}, "sha512-NUcwaKxUxWrZLpDG+z/xZaCgQITkA/Dv4V/T6bw7VON6l1Xz/VnrBqrYjZQ12TamKHzITTfOEIYUj48y2KXImA=="],
+    "pako": ["pako@1.0.11", "", {}, "sha512-4hLB8Py4zZce5s4yd9XzopqwVv/yGNhV1Bl8NTmCq1763HeK2+EwVTv+leGeL13Dnh2wfbqowVPXCIO0z4taYw=="],
 
     "parse-bmfont-ascii": ["parse-bmfont-ascii@1.0.6", "", {}, "sha512-U4RrVsUFCleIOBsIGYOMKjn9PavsGOXxbvYGtMOEfnId0SVNsgehXh1DxUdVPLoxd5mvcEtvmKs2Mmf0Mpa1ZA=="],
 
@@ -979,6 +1008,8 @@
 
     "path-data-parser": ["path-data-parser@0.1.0", "", {}, "sha512-NOnmBpt5Y2RWbuv0LMzsayp3lVylAHLPUTut412ZA3l+C4uw4ZVkQbjShYCQ8TCpUMdPapr4YjUqLYD6v68j+w=="],
 
+    "path-is-absolute": ["path-is-absolute@1.0.1", "", {}, "sha512-AVbw3UJ2e9bq64vSaS9Am0fje1Pa8pbGqTTsmXfaIiMpnr5DlDhfJOuLj9Sf95ZPVDAUerDfEk88MPmPe7UCQg=="],
+
     "path-key": ["path-key@3.1.1", "", {}, "sha512-ojmeN0qd+y0jszEtoY48r0Peq5dwMEkIlCOu6Q5f41lfkswXuKtYrhgoTpLnyIcHm24Uhqx+5Tqm2InSwLhE6Q=="],
 
     "path-to-regexp": ["path-to-regexp@8.3.0", "", {}, "sha512-7jdwVIRtsP8MYpdXSwOS0YdD0Du+qOoF/AEPIt88PcCFrZCzx41oxku1jD88hZBwbNUIEfpqvuhjFaMAqMTWnA=="],
@@ -1005,6 +1036,8 @@
 
     "process": ["process@0.11.10", "", {}, "sha512-cdGef/drWFoydD1JsMzuFf8100nZl+GT+yacc2bEced5f9Rjk4z+WtFUTBu9PhOi9j/jfmBPu0mMEY4wIdAF8A=="],
 
+    "process-nextick-args": ["process-nextick-args@2.0.1", "", {}, "sha512-3ouUOpQhtgrbOa17J7+uxOTpITYWaGP7/AhoR3+A+/1e9skrzelGi/dXzEYyvbxubEF6Wn2ypscTKiKJFFn1ag=="],
+
     "proper-lockfile": ["proper-lockfile@4.1.2", "", { "dependencies": { "graceful-fs": "^4.2.4", "retry": "^0.12.0", "signal-exit": "^3.0.2" } }, "sha512-TjNPblN4BwAWMXU8s9AEz4JmQxnD1NNL7bNOY/AKUzyamc379FWASUhc/K1pL2noVb+XmZKLL68cjzLsiOAMaA=="],
 
     "property-information": ["property-information@7.1.0", "", {}, "sha512-TwEZ+X+yCJmYfL7TPUOcvBZ4QfoT5YenQiJuX//0th53DE6w0xxLEtfK3iyryQFddXuvkIk51EEgrJQ0WJkOmQ=="],
@@ -1033,7 +1066,7 @@
 
     "react-tooltip": ["react-tooltip@5.30.1", "", { "dependencies": { "@floating-ui/dom": "^1.6.1", "classnames": "^2.3.0" }, "peerDependencies": { "react": ">=16.14.0", "react-dom": ">=16.14.0" } }, "sha512-1lSPLQXuVooePxadUpmcwLgOsF1mIty7UZTJ9XnyfX4drOzStYs4JMXnazcDLguQr41W5OUZddOp9kfvArdpEQ=="],
 
-    "readable-stream": ["readable-stream@4.7.0", "", { "dependencies": { "abort-controller": "^3.0.0", "buffer": "^6.0.3", "events": "^3.3.0", "process": "^0.11.10", "string_decoder": "^1.3.0" } }, "sha512-oIGGmcpTLwPga8Bn6/Z75SVaH1z5dUut2ibSyAMVhmUggWpmDn2dapB0n7f8nwaSiRtepAsfJyfXIO5DCVAODg=="],
+    "readable-stream": ["readable-stream@2.3.8", "", { "dependencies": { "core-util-is": "~1.0.0", "inherits": "~2.0.3", "isarray": "~1.0.0", "process-nextick-args": "~2.0.0", "safe-buffer": "~5.1.1", "string_decoder": "~1.1.1", "util-deprecate": "~1.0.1" } }, "sha512-8p0AUk4XODgIewSi0l8Epjs+EVnWiK7NoDIEGU0HhE7+ZyY8D1IMY7odu5lRrFXGg71L15KG8QrPmum45RTtdA=="],
 
     "readable-web-to-node-stream": ["readable-web-to-node-stream@3.0.4", "", { "dependencies": { "readable-stream": "^4.7.0" } }, "sha512-9nX56alTf5bwXQ3ZDipHJhusu9NTQJ/CVPtb/XHAJCXihZeitfJvIRS4GqQ/mfIoOE3IelHMrpayVrosdHBuLw=="],
 
@@ -1103,6 +1136,8 @@
 
     "set-cookie-parser": ["set-cookie-parser@2.7.1", "", {}, "sha512-IOc8uWeOZgnb3ptbCURJWNjWUPcO3ZnTTdzsurqERrP6nPyv+paC55vJM0LpOlT2ne+Ix+9+CRG1MNLlyZ4GjQ=="],
 
+    "setimmediate": ["setimmediate@1.0.5", "", {}, "sha512-MATJdZp8sLqDl/68LfQmbP8zKPLQNV6BIZoIgrscFDQ+RsvK/BxeDQOgyxKKoh0y/8h3BqVFnCqQ/gd+reiIXA=="],
+
     "setprototypeof": ["setprototypeof@1.2.0", "", {}, "sha512-E5LDX7Wrp85Kil5bhZv46j8jOeboKq5JMmYM3gVGdGH8xFpPWXUMsNrlODCrkoxMEeNi/XZIwuRvY4XNwYMJpw=="],
 
     "shebang-command": ["shebang-command@2.0.0", "", { "dependencies": { "shebang-regex": "^3.0.0" } }, "sha512-kHxr2zZpYtdmrN1qDjrrX/Z1rR1kG8Dx+gkpK1G4eXmvXswmcE1hTWBWYUzlraYw1/yZp6YuDY77YtvbN0dmDA=="],
@@ -1137,7 +1172,7 @@
 
     "string-width": ["string-width@8.1.0", "", { "dependencies": { "get-east-asian-width": "^1.3.0", "strip-ansi": "^7.1.0" } }, "sha512-Kxl3KJGb/gxkaUMOjRsQ8IrXiGW75O4E3RPjFIINOVH8AMl2SQ/yWdTzWwF3FevIX9LcMAjJW+GRwAlAbTSXdg=="],
 
-    "string_decoder": ["string_decoder@1.3.0", "", { "dependencies": { "safe-buffer": "~5.2.0" } }, "sha512-hkRX8U1WjJFd8LsDJ2yQ/wWWxaopEsABU1XfkM8A+j0+85JAGppt16cr1Whg6KIbb4okU6Mql6BOj+uup/wKeA=="],
+    "string_decoder": ["string_decoder@1.1.1", "", { "dependencies": { "safe-buffer": "~5.1.0" } }, "sha512-n/ShnvDi6FHbbVfviro+WojiFzv+s8MPMHBczVePfUpDJLwoLT0ht1l4YwBCbi8pJAveEEdnkHyPyTP/mzRfwg=="],
 
     "stringify-entities": ["stringify-entities@4.0.4", "", { "dependencies": { "character-entities-html4": "^2.0.0", "character-entities-legacy": "^3.0.0" } }, "sha512-IwfBptatlO+QCJUo19AqvrPNqlVMpW9YEL2LIVY+Rpv2qsjCGxaDLNRgeGsQWJhfItebuJhsGSLjaBbNSQ+ieg=="],
 
@@ -1185,10 +1220,16 @@
 
     "ts-dedent": ["ts-dedent@2.2.0", "", {}, "sha512-q5W7tVM71e2xjHZTlgfTDoPF/SmqKG5hddq9SzR49CH2hayqRKJtQ4mtRlSxKaJlR/+9rEM+mnBHf7I2/BQcpQ=="],
 
+    "turndown": ["turndown@7.2.4", "", { "dependencies": { "@mixmark-io/domino": "^2.2.0" } }, "sha512-I8yFsfRzmzK0WV1pNNOA4A7y4RDfFxPRxb3t+e3ui14qSGOxGtiSP6GjeX+Y6CHb7HYaFj7ECUD7VE5kQMZWGQ=="],
+
+    "turndown-plugin-gfm": ["turndown-plugin-gfm@1.0.2", "", {}, "sha512-vwz9tfvF7XN/jE0dGoBei3FXWuvll78ohzCZQuOb+ZjWrs3a0XhQVomJEb2Qh4VHTPNRO4GPZh0V7VRbiWwkRg=="],
+
     "type-is": ["type-is@2.0.1", "", { "dependencies": { "content-type": "^1.0.5", "media-typer": "^1.1.0", "mime-types": "^3.0.0" } }, "sha512-OZs6gsjF4vMp32qrCbiVSkrFmXtG/AZhY3t0iAMrMBiAZyV9oALtXO8hsrHbMXF9x6L3grlFuwW2oAz7cav+Gw=="],
 
     "ufo": ["ufo@1.6.1", "", {}, "sha512-9a4/uxlTWJ4+a5i0ooc1rU7C7YOw3wT+UGqdeNNHWnOF9qcMBgLRS+4IYUqbczewFx4mLEig6gawh7X6mFlEkA=="],
 
+    "underscore": ["underscore@1.13.8", "", {}, "sha512-DXtD3ZtEQzc7M8m4cXotyHR+FAS18C64asBYY5vqZexfYryNNnDc02W4hKg3rdQuqOYas1jkseX0+nZXjTXnvQ=="],
+
     "undici": ["undici@7.25.0", "", {}, "sha512-xXnp4kTyor2Zq+J1FfPI6Eq3ew5h6Vl0F/8d9XU5zZQf1tX9s2Su1/3PiMmUANFULpmksxkClamIZcaUqryHsQ=="],
 
     "undici-types": ["undici-types@7.25.0", "", {}, "sha512-AXNgS1Byr27fTI+2bsPEkV9CxkT8H6xNyRI68b3TatlZo3RkzlqQBLL+w7SmGPVpokjHbcuNVQUWE7FRTg+LRA=="],
@@ -1215,6 +1256,8 @@
 
     "utif2": ["utif2@4.1.0", "", { "dependencies": { "pako": "^1.0.11" } }, "sha512-+oknB9FHrJ7oW7A2WZYajOcv4FcDR4CfoGB0dPNfxbi4GO05RRnFmt5oa23+9w32EanrYcSJWspUiJkLMs+37w=="],
 
+    "util-deprecate": ["util-deprecate@1.0.2", "", {}, "sha512-EPD5q1uXyFxJpCrLnCc1nHnq3gOa6DZBocAIiI2TaSCA7VCJ1UJDMagCzIkXNsUYfD1daK//LTEQ8xiIbrHtcw=="],
+
     "uuid": ["uuid@11.1.0", "", { "bin": { "uuid": "dist/esm/bin/uuid" } }, "sha512-0/A9rDy9P7cJ+8w1c9WD9V//9Wj15Ce2MPz8Ri6032usz+NfePxx5AcN3bN+r6ZL6jEo066/yNYB3tn4pQEx+A=="],
 
     "vary": ["vary@1.1.2", "", {}, "sha512-BNGbWLfd0eUPabhkXUVm0j8uuvREyTh5ovRa/dyow/BqAbZJyC+5fU+IzQOzmAKzYqYRAISoRhdQr3eIZ/PXqg=="],
@@ -1259,7 +1302,7 @@
 
     "xml2js": ["xml2js@0.5.0", "", { "dependencies": { "sax": ">=0.6.0", "xmlbuilder": "~11.0.0" } }, "sha512-drPFnkQJik/O+uPKpqSgr22mpuFHqKdbS835iAQrUC73L2F5WkboIRd63ai/2Yg6I1jzifPFKH2NTK+cfglkIA=="],
 
-    "xmlbuilder": ["xmlbuilder@11.0.1", "", {}, "sha512-fDlsI/kFEx7gLvbecc0/ohLG50fugQp8ryHzMTuW9vSa1GJ0XYWKnhsUx7oie3G98+r56aTQIUB4kht42R3JvA=="],
+    "xmlbuilder": ["xmlbuilder@10.1.1", "", {}, "sha512-OyzrcFLL/nb6fMGHbiRDuPup9ljBycsdCypwuyg5AAHvyWzGfChJpCXMG88AGTIMFhGZ9RccFN1e6lhg3hkwKg=="],
 
     "xmlchars": ["xmlchars@2.2.0", "", {}, "sha512-JZnDKK8B0RCDw84FNdDAIpZK+JuJw+s7Lz8nksI7SIuU3UXJJslUthsi+uWBUYOwPFwW7W7PRLRfUKpxjtjFCw=="],
 
@@ -1333,14 +1376,22 @@
 
     "react-router/cookie": ["cookie@1.0.2", "", {}, "sha512-9Kr/j4O16ISv8zBBhJoi4bXOYNTkFLOqSL3UDB0njXxCXNezjeyVrJyGOWtgfs/q2km1gwBcfH8q1yEGoMYunA=="],
 
+    "readable-stream/safe-buffer": ["safe-buffer@5.1.2", "", {}, "sha512-Gd2UZBJDkXlY7GbJxfsE8/nvKkUEU1G38c1siN6QP6a9PT9MmHB8GnpscSmMJSoF8LOIrt8ud/wPtojys4G6+g=="],
+
+    "readable-web-to-node-stream/readable-stream": ["readable-stream@4.7.0", "", { "dependencies": { "abort-controller": "^3.0.0", "buffer": "^6.0.3", "events": "^3.3.0", "process": "^0.11.10", "string_decoder": "^1.3.0" } }, "sha512-oIGGmcpTLwPga8Bn6/Z75SVaH1z5dUut2ibSyAMVhmUggWpmDn2dapB0n7f8nwaSiRtepAsfJyfXIO5DCVAODg=="],
+
     "refractor/@types/hast": ["@types/hast@2.3.10", "", { "dependencies": { "@types/unist": "^2" } }, "sha512-McWspRw8xx8J9HurkVBfYj0xKoE25tOFlHGdx4MJ5xORQrMGZNqJhVQWaIbm6Oyla5kYOXtDiopzKRJzEOkwJw=="],
 
     "restore-cursor/signal-exit": ["signal-exit@4.1.0", "", {}, "sha512-bzyZ1e88w9O1iNJbKnOlvYTrWPDl46O1bG0D3XInv+9tkPrxrN8jUUTiFlDkkmKWgn1M6CfIA13SuGqOa9Korw=="],
 
-    "utif2/pako": ["pako@1.0.11", "", {}, "sha512-4hLB8Py4zZce5s4yd9XzopqwVv/yGNhV1Bl8NTmCq1763HeK2+EwVTv+leGeL13Dnh2wfbqowVPXCIO0z4taYw=="],
+    "string_decoder/safe-buffer": ["safe-buffer@5.1.2", "", {}, "sha512-Gd2UZBJDkXlY7GbJxfsE8/nvKkUEU1G38c1siN6QP6a9PT9MmHB8GnpscSmMJSoF8LOIrt8ud/wPtojys4G6+g=="],
+
+    "unicode-trie/pako": ["pako@0.2.9", "", {}, "sha512-NUcwaKxUxWrZLpDG+z/xZaCgQITkA/Dv4V/T6bw7VON6l1Xz/VnrBqrYjZQ12TamKHzITTfOEIYUj48y2KXImA=="],
 
     "wrap-ansi/string-width": ["string-width@7.2.0", "", { "dependencies": { "emoji-regex": "^10.3.0", "get-east-asian-width": "^1.0.0", "strip-ansi": "^7.1.0" } }, "sha512-tsaTIkKW9b4N+AEj+SVA+WhJzV7/zMhcSu78mLKWSk7cXMOSHsBKFWUs0fWwq8QyK3MgJBQRX6Gbi4kYbdvGkQ=="],
 
+    "xml2js/xmlbuilder": ["xmlbuilder@11.0.1", "", {}, "sha512-fDlsI/kFEx7gLvbecc0/ohLG50fugQp8ryHzMTuW9vSa1GJ0XYWKnhsUx7oie3G98+r56aTQIUB4kht42R3JvA=="],
+
     "@tailwindcss/oxide-wasm32-wasi/@emnapi/core/@emnapi/wasi-threads": ["@emnapi/wasi-threads@1.2.1", "", { "dependencies": { "tslib": "^2.4.0" } }, "sha512-uTII7OYF+/Mes/MrcIOYp5yOtSMLBWSIoLPpcgwipoiKbli6k322tcoFsxoIIxPDqW01SQGAgko4EzZi2BNv2w=="],
 
     "@tailwindcss/oxide-wasm32-wasi/@napi-rs/wasm-runtime/@emnapi/core": ["@emnapi/core@1.7.1", "", { "dependencies": { "@emnapi/wasi-threads": "1.1.0", "tslib": "^2.4.0" } }, "sha512-o1uhUASyo921r2XtHYOHy7gdkGLge8ghBEQHMWmyJFoXlpU58kIrhhN3w26lpQb6dspetweapMn2CSNwQ8I4wg=="],
@@ -1365,6 +1416,8 @@
 
     "mlly/pkg-types/confbox": ["confbox@0.1.8", "", {}, "sha512-RMtmw0iFkeR4YV+fUOSucriAQNb9g8zFR52MWCtl+cCZOFRNL6zeB395vPzFhEjjn4fMxXudmELnl/KF/WrK6w=="],
 
+    "readable-web-to-node-stream/readable-stream/string_decoder": ["string_decoder@1.3.0", "", { "dependencies": { "safe-buffer": "~5.2.0" } }, "sha512-hkRX8U1WjJFd8LsDJ2yQ/wWWxaopEsABU1XfkM8A+j0+85JAGppt16cr1Whg6KIbb4okU6Mql6BOj+uup/wKeA=="],
+
     "refractor/@types/hast/@types/unist": ["@types/unist@2.0.11", "", {}, "sha512-CmBKiL6NNo/OqgmMn95Fk9Whlp2mtvIv+KNpQKN2F4SjvrEesubTRWGYSg+BnWZOnlCaSTU1sMpsBOzgbYhnsA=="],
   }
 }
diff --git a/package.json b/package.json
index b75168560..2be12940d 100644
--- a/package.json
+++ b/package.json
@@ -46,7 +46,10 @@
     "react-dom": "19.2.5",
     "react-router-dom": "7.14.1",
     "react-tooltip": "5.30.1",
-    "tailwindcss": "4.2.2"
+    "tailwindcss": "4.2.2",
+    "turndown": "7.2.4",
+    "turndown-plugin-gfm": "1.0.2",
+    "mammoth": "1.12.0"
   },
   "scripts": {
     "test": "bun test",
diff --git a/src/core/assets.ts b/src/core/assets.ts
new file mode 100644
index 000000000..bea2a4659
--- /dev/null
+++ b/src/core/assets.ts
@@ -0,0 +1,194 @@
+import { randomUUID } from "node:crypto";
+import { mkdir, readdir, rm, stat } from "node:fs/promises";
+import { join } from "node:path";
+
+export interface UploadResult {
+	url: string;
+}
+
+export class ClientError extends Error {
+	constructor(message: string) {
+		super(message);
+		this.name = "ClientError";
+	}
+}
+
+export class AssetManager {
+	constructor(private assetsRoot: string) {}
+
+	private get tempDir(): string {
+		return join(this.assetsRoot, ".temp");
+	}
+
+	private get pasteDir(): string {
+		return join(this.assetsRoot, "paste");
+	}
+
+	private resolveExtFromMime(mime: string): string {
+		const map: Record<string, string> = {
+			"image/png": "png",
+			"image/jpeg": "jpg",
+			"image/gif": "gif",
+			"image/webp": "webp",
+			"image/svg+xml": "svg",
+		};
+		return map[mime] || "png";
+	}
+
+	async uploadFile(file: File, isTemp = false): Promise<UploadResult> {
+		const buffer = new Uint8Array(await file.arrayBuffer());
+		const nameMatch = file.name.match(/\.([^./]+)$/);
+		const ext = nameMatch ? nameMatch[1]!.toLowerCase() : this.resolveExtFromMime(file.type);
+		return this.saveBuffer(buffer, ext, isTemp);
+	}
+
+	async uploadFromDataUri(dataUri: string, isTemp = false): Promise<UploadResult> {
+		const match = dataUri.match(/^data:([^;]+);base64,(.+)$/);
+		if (!match) {
+			throw new ClientError("Invalid data URI");
+		}
+		const mime = match[1]!;
+		const base64 = match[2]!;
+		const buffer = Uint8Array.from(atob(base64), (c) => c.charCodeAt(0));
+		return this.saveBuffer(buffer, this.resolveExtFromMime(mime), isTemp);
+	}
+
+	async uploadFromUrl(imageUrl: string, isTemp = false): Promise<UploadResult> {
+		const blob = await this.downloadImage(imageUrl);
+		if (!blob) {
+			throw new ClientError("Failed to download image");
+		}
+		const buffer = new Uint8Array(await blob.arrayBuffer());
+		return this.saveBuffer(buffer, this.resolveExtFromMime(blob.type), isTemp);
+	}
+
+	async promote(urls: string[]): Promise<Record<string, string>> {
+		const pasteDir = this.pasteDir;
+		await mkdir(pasteDir, { recursive: true });
+		const result: Record<string, string> = {};
+
+		for (const url of urls) {
+			if (typeof url !== "string" || !url.startsWith("/assets/.temp/")) continue;
+			const filename = url.slice("/assets/.temp/".length);
+			if (filename.includes("..") || filename.includes("/") || filename.includes("\\")) continue;
+
+			const sourcePath = join(this.assetsRoot, ".temp", filename);
+			const destPath = join(pasteDir, filename);
+
+			const sourceFile = Bun.file(sourcePath);
+			if (!(await sourceFile.exists())) continue;
+
+			await Bun.write(destPath, sourceFile);
+			await rm(sourcePath);
+			result[url] = `/assets/paste/${filename}`;
+		}
+		return result;
+	}
+
+	async cleanup(options?: { maxAgeMs?: number }): Promise<{ removed: number }> {
+		const maxAgeMs = options?.maxAgeMs ?? 30 * 60 * 1000;
+		const entries = await readdir(this.tempDir).catch(() => [] as string[]);
+		if (entries.length === 0) return { removed: 0 };
+
+		const now = Date.now();
+		let removed = 0;
+
+		for (const name of entries) {
+			const filePath = join(this.tempDir, name);
+			try {
+				const info = await stat(filePath);
+				if (!info.isFile()) continue;
+				if (now - info.mtimeMs > maxAgeMs) {
+					await rm(filePath);
+					removed++;
+				}
+			} catch {
+				// ignore per-file errors
+			}
+		}
+		return { removed };
+	}
+
+	async downloadImage(url: string): Promise<Blob | null> {
+		try {
+			const parsed = new URL(url);
+			if (parsed.protocol !== "http:" && parsed.protocol !== "https:") return null;
+
+			const hostname = parsed.hostname.toLowerCase();
+			if (hostname === "localhost" || hostname === "127.0.0.1" || hostname === "::1") return null;
+			if (/^10\./.test(hostname)) return null;
+			if (/^172\.(1[6-9]|2\d|3[01])\./.test(hostname)) return null;
+			if (/^192\.168\./.test(hostname)) return null;
+
+			const controller = new AbortController();
+			const timeout = setTimeout(() => controller.abort(), 30000);
+
+			let currentUrl = url;
+			let redirects = 0;
+			const maxRedirects = 3;
+
+			while (redirects <= maxRedirects) {
+				const response = await fetch(currentUrl, {
+					signal: controller.signal,
+					redirect: "manual",
+				});
+
+				if (response.status >= 300 && response.status < 400) {
+					const location = response.headers.get("location");
+					if (!location) break;
+					currentUrl = new URL(location, currentUrl).href;
+					redirects++;
+					const redirectParsed = new URL(currentUrl);
+					if (redirectParsed.protocol !== "http:" && redirectParsed.protocol !== "https:") break;
+					const redirectHost = redirectParsed.hostname.toLowerCase();
+					if (redirectHost === "localhost" || redirectHost === "127.0.0.1" || redirectHost === "::1") break;
+					if (/^10\./.test(redirectHost)) break;
+					if (/^172\.(1[6-9]|2\d|3[01])\./.test(redirectHost)) break;
+					if (/^192\.168\./.test(redirectHost)) break;
+					continue;
+				}
+
+				clearTimeout(timeout);
+
+				if (!response.ok) return null;
+
+				const contentType = response.headers.get("content-type") || "";
+				if (!contentType.startsWith("image/")) return null;
+
+				const contentLength = response.headers.get("content-length");
+				if (contentLength) {
+					const size = Number.parseInt(contentLength, 10);
+					if (!Number.isNaN(size) && size > 20 * 1024 * 1024) return null;
+				}
+
+				const blob = await response.blob();
+				if (blob.size > 20 * 1024 * 1024) return null;
+				return blob;
+			}
+
+			clearTimeout(timeout);
+			return null;
+		} catch {
+			return null;
+		}
+	}
+
+	private async saveBuffer(buffer: Uint8Array, ext: string, isTemp: boolean): Promise<UploadResult> {
+		if (buffer.length === 0) {
+			throw new ClientError("Empty file");
+		}
+		if (buffer.length > 20 * 1024 * 1024) {
+			throw new ClientError("File too large (max 20 MB)");
+		}
+
+		const targetDir = isTemp ? this.tempDir : this.pasteDir;
+		await mkdir(targetDir, { recursive: true });
+
+		const filename = `${randomUUID()}.${ext}`;
+		const filePath = join(targetDir, filename);
+		await Bun.write(filePath, buffer);
+
+		const relPath = isTemp ? `.temp/${filename}` : `paste/${filename}`;
+		return { url: `/assets/${relPath}` };
+	}
+}
diff --git a/src/core/backlog.ts b/src/core/backlog.ts
index 2d3a0d52e..1a7821341 100644
--- a/src/core/backlog.ts
+++ b/src/core/backlog.ts
@@ -1,5 +1,5 @@
 import { rename as moveFile, unlink } from "node:fs/promises";
-import { join } from "node:path";
+import { dirname, join } from "node:path";
 import { DEFAULT_STATUSES, FALLBACK_STATUS } from "../constants/index.ts";
 import { FileSystem } from "../file-system/operations.ts";
 import { GitOperations } from "../git/operations.ts";
@@ -57,6 +57,7 @@ import { ContentStore } from "./content-store.ts";
 import { migrateDraftPrefixes, needsDraftPrefixMigration } from "./prefix-migration.ts";
 import { calculateNewOrdinal, DEFAULT_ORDINAL_STEP, resolveOrdinalConflicts } from "./reorder.ts";
 import { SearchService } from "./search-service.ts";
+import { AssetManager } from "./assets.ts";
 import { computeSequences, planMoveToSequence, planMoveToUnsequenced } from "./sequences.ts";
 import {
 	type BranchTaskStateEntry,
@@ -173,6 +174,7 @@ function getActiveAndCompletedIdsFromStateMap(latestState: Map<string, BranchTas
 export class Core {
 	public fs: FileSystem;
 	public git: GitOperations;
+	public assets: AssetManager;
 	private contentStore?: ContentStore;
 	private searchService?: SearchService;
 	private readonly enableWatchers: boolean;
@@ -180,6 +182,7 @@ export class Core {
 	constructor(projectRoot: string, options?: { enableWatchers?: boolean }) {
 		this.fs = new FileSystem(projectRoot);
 		this.git = new GitOperations(projectRoot, null, () => this.fs.loadConfig());
+		this.assets = new AssetManager(join(dirname(this.fs.docsDir), "assets"));
 		// Disable watchers by default for CLI commands (non-interactive)
 		// Interactive modes (TUI, browser, MCP) should explicitly pass enableWatchers: true
 		this.enableWatchers = options?.enableWatchers ?? false;
diff --git a/src/core/docx-converter.ts b/src/core/docx-converter.ts
new file mode 100644
index 000000000..f9cc1732d
--- /dev/null
+++ b/src/core/docx-converter.ts
@@ -0,0 +1,32 @@
+import mammoth from "mammoth";
+import type { AssetManager } from "./assets.ts";
+
+export interface DocxConvertResult {
+	html: string;
+	images: { tempUrl: string; alt: string }[];
+	messages: string[];
+}
+
+export async function convertDocxToMarkdown(buffer: Buffer, assetManager: AssetManager): Promise<DocxConvertResult> {
+	const images: { tempUrl: string; alt: string }[] = [];
+
+	const result = await mammoth.convertToHtml(
+		{ buffer },
+		{
+			convertImage: mammoth.images.imgElement(async (image) => {
+				const imageBuffer = await image.readAsArrayBuffer();
+				const blob = new Blob([new Uint8Array(imageBuffer)], { type: image.contentType });
+				const file = new File([blob], "image.png", { type: image.contentType });
+				const uploadResult = await assetManager.uploadFile(file, true);
+				images.push({ tempUrl: uploadResult.url, alt: "" });
+				return { src: uploadResult.url };
+			}),
+		},
+	);
+
+	return {
+		html: result.value,
+		images,
+		messages: result.messages.map((m) => m.message),
+	};
+}
diff --git a/src/file-system/operations.ts b/src/file-system/operations.ts
index 160d075de..ac4c759d1 100644
--- a/src/file-system/operations.ts
+++ b/src/file-system/operations.ts
@@ -1,5 +1,5 @@
-import { mkdir, rename, unlink } from "node:fs/promises";
-import { dirname, join } from "node:path";
+import { mkdir, rename, stat, unlink } from "node:fs/promises";
+import { dirname, isAbsolute, join, relative, resolve } from "node:path";
 import matter from "gray-matter";
 import lockfile from "proper-lockfile";
 import { DEFAULT_DIRECTORIES, DEFAULT_FILES, DEFAULT_STATUSES, FALLBACK_STATUS } from "../constants/index.ts";
@@ -1605,6 +1605,76 @@ ${description || `Milestone: ${title}`}`,
 		return changed ? escaped : undefined;
 	}
 
+	async readProjectFile(rawPath: string): Promise<{
+		content: string;
+		path: string;
+		lineStart?: number;
+		lineEnd?: number;
+		totalLines: number;
+		isMarkdown: boolean;
+	}> {
+		const MAX_FILE_SIZE = 5 * 1024 * 1024; // 5MB
+
+		const lineRangeMatch = rawPath.match(/^(.+?)(?::(\d+)(?:-(\d+))?)?$/);
+		const filePath = lineRangeMatch?.[1] ?? rawPath;
+		const lineStart = lineRangeMatch?.[2] ? Number.parseInt(lineRangeMatch[2], 10) : undefined;
+		const lineEnd = lineRangeMatch?.[3] ? Number.parseInt(lineRangeMatch[3], 10) : lineStart;
+
+		const rootDir = resolve(this.projectRoot);
+		const targetPath = resolve(join(rootDir, filePath));
+
+		// Robust containment check: reject traversal, absolute paths, and root itself
+		const rel = relative(rootDir, targetPath);
+		const isInside = !rel.startsWith("..") && !isAbsolute(rel);
+		if (!isInside || isAbsolute(filePath)) {
+			throw new Error("Access denied");
+		}
+
+		let fileStats: ReturnType<typeof stat> extends Promise<infer T> ? T : never;
+		try {
+			fileStats = await stat(targetPath);
+		} catch {
+			throw new Error("File not found");
+		}
+		if (fileStats.isDirectory()) {
+			throw new Error("Path is a directory");
+		}
+		if (fileStats.size > MAX_FILE_SIZE) {
+			throw new Error("File too large");
+		}
+
+		const file = Bun.file(targetPath);
+		const fullContent = await file.text();
+		const allLines = fullContent.split(/\r?\n/);
+		const totalLines = allLines.length;
+
+		let content: string;
+		let start: number | undefined;
+		let end: number | undefined;
+
+		if (lineStart !== undefined && lineEnd !== undefined) {
+			start = Math.max(1, lineStart);
+			end = Math.min(totalLines, lineEnd);
+			if (start > end) {
+				throw new Error("Invalid line range");
+			}
+			content = allLines.slice(start - 1, end).join("\n");
+		} else {
+			content = fullContent;
+		}
+
+		const isMarkdown = targetPath.toLowerCase().endsWith(".md");
+
+		return {
+			content,
+			path: filePath,
+			lineStart: start,
+			lineEnd: end,
+			totalLines,
+			isMarkdown,
+		};
+	}
+
 	private normalizeDefinitionOfDone(definitionOfDone: unknown): string[] | undefined {
 		if (!Array.isArray(definitionOfDone)) {
 			return undefined;
diff --git a/src/server/index.ts b/src/server/index.ts
index bb13bb4f6..255d4b11b 100644
--- a/src/server/index.ts
+++ b/src/server/index.ts
@@ -3,6 +3,7 @@ import type { Server, ServerWebSocket } from "bun";
 import { $ } from "bun";
 import { Core } from "../core/backlog.ts";
 import type { ContentStore } from "../core/content-store.ts";
+import { convertDocxToMarkdown } from "../core/docx-converter.ts";
 import { initializeProject } from "../core/init.ts";
 import type { SearchService } from "../core/search-service.ts";
 import { getTaskStatistics } from "../core/statistics.ts";
@@ -297,6 +298,7 @@ export class BacklogServer {
 
 		try {
 			await this.ensureServicesReady();
+			void this.cleanupTempAssets();
 			const serveOptions = {
 				port: finalPort,
 				development: process.env.NODE_ENV === "development",
@@ -405,6 +407,18 @@ export class BacklogServer {
 					"/api/search": {
 						GET: async (req: Request) => await this.handleSearch(req),
 					},
+					"/api/file-content": {
+						GET: async (req: Request) => await this.handleGetFileContent(req),
+					},
+					"/api/upload": {
+						POST: async (req: Request) => await this.handleUpload(req),
+					},
+					"/api/assets/promote": {
+						POST: async (req: Request) => await this.handlePromoteAssets(req),
+					},
+					"/api/docx/convert": {
+						POST: async (req: Request) => await this.handleConvertDocx(req),
+					},
 					"/sequences": {
 						GET: async () => await this.handleGetSequences(),
 					},
@@ -1673,6 +1687,32 @@ export class BacklogServer {
 		}
 	}
 
+	private async handleGetFileContent(req: Request): Promise<Response> {
+		try {
+			const url = new URL(req.url);
+			const rawPath = url.searchParams.get("path") || "";
+			if (!rawPath) {
+				return Response.json({ error: "path parameter is required" }, { status: 400 });
+			}
+
+			const result = await this.core.filesystem.readProjectFile(rawPath);
+			return Response.json(result);
+		} catch (error) {
+			console.error("Error reading file:", error);
+			const message = error instanceof Error ? error.message : "Failed to read file";
+			if (message === "Access denied") {
+				return Response.json({ error: message }, { status: 403 });
+			}
+			if (message === "File not found" || message === "Path is a directory") {
+				return Response.json({ error: message }, { status: 404 });
+			}
+			if (message === "Invalid line range" || message === "File too large") {
+				return Response.json({ error: message }, { status: 400 });
+			}
+			return Response.json({ error: message }, { status: 500 });
+		}
+	}
+
 	private async handleGetStatus(): Promise<Response> {
 		try {
 			const config = await this.core.filesystem.loadConfig();
@@ -1763,4 +1803,93 @@ export class BacklogServer {
 			return Response.json({ error: message }, { status: 500 });
 		}
 	}
+
+	private async handleUpload(req: Request): Promise<Response> {
+		try {
+			const url = new URL(req.url);
+			const isTemp = url.searchParams.get("temp") === "1";
+			const contentType = req.headers.get("content-type") || "";
+
+			if (contentType.startsWith("multipart/form-data")) {
+				const formData = await req.formData();
+				const file = formData.get("file");
+				if (!(file instanceof File)) {
+					return Response.json({ error: "No file provided" }, { status: 400 });
+				}
+				const result = await this.core.assets.uploadFile(file, isTemp);
+				return Response.json(result);
+			}
+
+			if (contentType.startsWith("application/json")) {
+				const body = await req.json();
+				if (typeof body.dataUri === "string") {
+					const result = await this.core.assets.uploadFromDataUri(body.dataUri, isTemp);
+					return Response.json(result);
+				}
+				if (typeof body.url === "string") {
+					const result = await this.core.assets.uploadFromUrl(body.url, isTemp);
+					return Response.json(result);
+				}
+				return Response.json({ error: "Expected file, url, or dataUri" }, { status: 400 });
+			}
+
+			return Response.json({ error: "Unsupported content type" }, { status: 400 });
+		} catch (error) {
+			console.error("Error uploading file:", error);
+			const message = error instanceof Error ? error.message : "Upload failed";
+			const isClientError = error instanceof Error && error.name === "ClientError";
+			return Response.json({ error: message }, { status: isClientError ? 400 : 500 });
+		}
+	}
+
+	private async handlePromoteAssets(req: Request): Promise<Response> {
+		try {
+			const body = await req.json();
+			const urls = Array.isArray(body.urls) ? body.urls : [];
+			const result = await this.core.assets.promote(urls);
+			return Response.json(result);
+		} catch (error) {
+			console.error("Error promoting assets:", error);
+			const message = error instanceof Error ? error.message : "Promote failed";
+			return Response.json({ error: message }, { status: 500 });
+		}
+	}
+
+	private async handleConvertDocx(req: Request): Promise<Response> {
+		try {
+			const contentType = req.headers.get("content-type") || "";
+			if (!contentType.startsWith("multipart/form-data")) {
+				return Response.json({ error: "Expected multipart/form-data" }, { status: 400 });
+			}
+
+			const formData = await req.formData();
+			const file = formData.get("file");
+			if (!(file instanceof File)) {
+				return Response.json({ error: "No file provided" }, { status: 400 });
+			}
+
+			if (!file.name.toLowerCase().endsWith(".docx")) {
+				return Response.json({ error: "Only .docx files are supported" }, { status: 400 });
+			}
+
+			const buffer = Buffer.from(await file.arrayBuffer());
+			const result = await convertDocxToMarkdown(buffer, this.core.assets);
+			return Response.json(result);
+		} catch (error) {
+			console.error("Error converting docx:", error);
+			const message = error instanceof Error ? error.message : "Conversion failed";
+			return Response.json({ error: message }, { status: 500 });
+		}
+	}
+
+	private async cleanupTempAssets(): Promise<void> {
+		try {
+			const { removed } = await this.core.assets.cleanup();
+			if (removed > 0) {
+				console.log(`🧹 Cleaned up ${removed} temporary asset(s) older than 30 min`);
+			}
+		} catch {
+			// ignore cleanup errors — don't block server start
+		}
+	}
 }
diff --git a/src/test/assets.test.ts b/src/test/assets.test.ts
new file mode 100644
index 000000000..954bb8d85
--- /dev/null
+++ b/src/test/assets.test.ts
@@ -0,0 +1,113 @@
+import { describe, expect, it, beforeEach, afterEach } from "bun:test";
+import { mkdir, utimes } from "node:fs/promises";
+import { join } from "node:path";
+import { AssetManager } from "../core/assets.ts";
+import { createUniqueTestDir, safeCleanup } from "./test-utils.ts";
+
+let TEST_DIR: string;
+let assetsRoot: string;
+let manager: AssetManager;
+
+
+describe("AssetManager", () => {
+	beforeEach(async () => {
+		TEST_DIR = createUniqueTestDir("assets");
+		assetsRoot = join(TEST_DIR, "assets");
+		await mkdir(join(assetsRoot, ".temp"), { recursive: true });
+		manager = new AssetManager(assetsRoot);
+	});
+
+	afterEach(async () => {
+		await safeCleanup(TEST_DIR);
+	});
+
+	it("uploads a file to temp directory", async () => {
+		const file = new File(["fake-png"], "screenshot.png", { type: "image/png" });
+		const result = await manager.uploadFile(file, true);
+		expect(result.url).toMatch(/^\/assets\/\.temp\/[\w-]+\.png$/);
+
+		const filename = result.url.replace("/assets/.temp/", "");
+		const filePath = join(assetsRoot, ".temp", filename);
+		expect(await Bun.file(filePath).exists()).toBe(true);
+		expect(await Bun.file(filePath).text()).toBe("fake-png");
+	});
+
+	it("uploads from a data URI", async () => {
+		const base64 = btoa("hello-image");
+		const dataUri = `data:image/png;base64,${base64}`;
+		const result = await manager.uploadFromDataUri(dataUri, true);
+		expect(result.url).toMatch(/^\/assets\/\.temp\/[\w-]+\.png$/);
+
+		const filename = result.url.replace("/assets/.temp/", "");
+		const filePath = join(assetsRoot, ".temp", filename);
+		expect(await Bun.file(filePath).exists()).toBe(true);
+	});
+
+	it("rejects invalid data URI", async () => {
+		await expect(manager.uploadFromDataUri("not-a-data-uri", true)).rejects.toThrow("Invalid data URI");
+	});
+
+	it("rejects empty file", async () => {
+		const file = new File([], "empty.png", { type: "image/png" });
+		await expect(manager.uploadFile(file, true)).rejects.toThrow("Empty file");
+	});
+
+	it("promotes temp assets to paste directory", async () => {
+		const file = new File(["promote-me"], "test.png", { type: "image/png" });
+		const upload = await manager.uploadFile(file, true);
+
+		const mapping = await manager.promote([upload.url]);
+		expect(mapping[upload.url]).toMatch(/^\/assets\/paste\/[\w-]+\.png$/);
+		const pasteUrl = mapping[upload.url];
+		if (!pasteUrl) throw new Error("promote returned empty mapping");
+
+		const tempPath = join(assetsRoot, ".temp", upload.url.replace("/assets/.temp/", ""));
+		const pastePath = join(assetsRoot, "paste", pasteUrl.replace("/assets/paste/", ""));
+
+		expect(await Bun.file(tempPath).exists()).toBe(false);
+		expect(await Bun.file(pastePath).exists()).toBe(true);
+	});
+
+	it("ignores invalid URLs during promote", async () => {
+		const mapping = await manager.promote(["/assets/paste/already.png", "/assets/../escape.png"]);
+		expect(Object.keys(mapping)).toHaveLength(0);
+	});
+
+	it("cleans up old temp files", async () => {
+		const file = new File(["old"], "old.png", { type: "image/png" });
+		const upload = await manager.uploadFile(file, true);
+		const filePath = join(assetsRoot, ".temp", upload.url.replace("/assets/.temp/", ""));
+
+		const agedTime = new Date(Date.now() - 31 * 60 * 1000);
+		await utimes(filePath, agedTime, agedTime);
+
+		const result = await manager.cleanup({ maxAgeMs: 30 * 60 * 1000 });
+		expect(result.removed).toBe(1);
+		expect(await Bun.file(filePath).exists()).toBe(false);
+	});
+
+	it("skips fresh files during cleanup", async () => {
+		const file = new File(["fresh"], "fresh.png", { type: "image/png" });
+		const upload = await manager.uploadFile(file, true);
+		const filePath = join(assetsRoot, ".temp", upload.url.replace("/assets/.temp/", ""));
+
+		const result = await manager.cleanup({ maxAgeMs: 30 * 60 * 1000 });
+		expect(result.removed).toBe(0);
+		expect(await Bun.file(filePath).exists()).toBe(true);
+	});
+
+	it("blocks download from localhost", async () => {
+		const result = await manager.downloadImage("http://localhost:8080/image.png");
+		expect(result).toBeNull();
+	});
+
+	it("blocks download from private IP", async () => {
+		const result = await manager.downloadImage("http://192.168.1.1/image.png");
+		expect(result).toBeNull();
+	});
+
+	it("blocks non-http protocols", async () => {
+		const result = await manager.downloadImage("ftp://example.com/image.png");
+		expect(result).toBeNull();
+	});
+});
diff --git a/src/test/filesystem.test.ts b/src/test/filesystem.test.ts
index 34e6f1d50..9155e14ba 100644
--- a/src/test/filesystem.test.ts
+++ b/src/test/filesystem.test.ts
@@ -907,4 +907,54 @@ Invalid content`,
 			expect(filename?.includes("--")).toBe(false);
 		});
 	});
+
+	describe("readProjectFile", () => {
+		it("reads a valid file within project root", async () => {
+			const testFile = join(TEST_DIR, "src", "test.ts");
+			await mkdir(join(TEST_DIR, "src"), { recursive: true });
+			await Bun.write(testFile, "line 1\nline 2\nline 3");
+			const result = await filesystem.readProjectFile("src/test.ts");
+			expect(result.content).toBe("line 1\nline 2\nline 3");
+			expect(result.totalLines).toBe(3);
+			expect(result.isMarkdown).toBe(false);
+		});
+
+		it("rejects sibling-prefix traversal", async () => {
+			await mkdir(join(TEST_DIR, "project-secret"), { recursive: true });
+			await Bun.write(join(TEST_DIR, "project-secret", "secret.txt"), "secret");
+			await expect(filesystem.readProjectFile("../project-secret/secret.txt")).rejects.toThrow("Access denied");
+		});
+
+		it("rejects absolute paths", async () => {
+			await expect(filesystem.readProjectFile("/etc/passwd")).rejects.toThrow("Access denied");
+		});
+
+		it("rejects .. traversal", async () => {
+			await expect(filesystem.readProjectFile("../../../etc/passwd")).rejects.toThrow("Access denied");
+		});
+
+		it("supports line ranges", async () => {
+			const testFile = join(TEST_DIR, "file.ts");
+			await Bun.write(testFile, "a\nb\nc\nd\ne\n");
+			const result = await filesystem.readProjectFile("file.ts:2-4");
+			expect(result.content).toBe("b\nc\nd");
+			expect(result.lineStart).toBe(2);
+			expect(result.lineEnd).toBe(4);
+		});
+
+		it("rejects non-existent files", async () => {
+			await expect(filesystem.readProjectFile("missing.txt")).rejects.toThrow("File not found");
+		});
+
+		it("rejects directories", async () => {
+			await mkdir(join(TEST_DIR, "subdir"), { recursive: true });
+			await expect(filesystem.readProjectFile("subdir")).rejects.toThrow("Path is a directory");
+		});
+
+		it("rejects oversized files", async () => {
+			const bigFile = join(TEST_DIR, "big.txt");
+			await Bun.write(bigFile, "x".repeat(6 * 1024 * 1024));
+			await expect(filesystem.readProjectFile("big.txt")).rejects.toThrow("File too large");
+		});
+	});
 });
diff --git a/src/test/server-docx-convert.test.ts b/src/test/server-docx-convert.test.ts
new file mode 100644
index 000000000..13cfd2fbb
--- /dev/null
+++ b/src/test/server-docx-convert.test.ts
@@ -0,0 +1,136 @@
+import { afterEach, beforeEach, describe, expect, it } from "bun:test";
+import { dirname, join } from "node:path";
+import { FileSystem } from "../file-system/operations.ts";
+import { BacklogServer } from "../server/index.ts";
+import { createUniqueTestDir, retry, safeCleanup } from "./test-utils.ts";
+
+let TEST_DIR: string;
+let filesystem: FileSystem;
+let server: BacklogServer | null = null;
+let serverPort = 0;
+
+async function fetchWithTimeout(path: string, options: RequestInit = {}, timeoutMs = 1000): Promise<Response> {
+	const controller = new AbortController();
+	const timeout = setTimeout(() => controller.abort(), timeoutMs);
+	try {
+		return await fetch(`http://127.0.0.1:${serverPort}${path}`, { ...options, signal: controller.signal });
+	} finally {
+		clearTimeout(timeout);
+	}
+}
+
+describe("BacklogServer docx convert", () => {
+	beforeEach(async () => {
+		TEST_DIR = createUniqueTestDir("server-docx");
+		filesystem = new FileSystem(TEST_DIR);
+		await filesystem.ensureBacklogStructure();
+
+		await filesystem.saveConfig({
+			projectName: "Docx Test",
+			statuses: ["To Do", "In Progress", "Done"],
+			labels: [],
+			milestones: [],
+			dateFormat: "YYYY-MM-DD",
+			remoteOperations: false,
+		});
+
+		server = new BacklogServer(TEST_DIR);
+		await server.start(0, false);
+		const port = server.getPort();
+		expect(port).not.toBeNull();
+		serverPort = port ?? 0;
+
+		await retry(
+			async () => {
+				const res = await fetchWithTimeout("/api/status", {}, 500);
+				if (!res.ok) throw new Error("server not ready");
+				return true;
+			},
+			10,
+			50,
+		);
+	});
+
+	afterEach(async () => {
+		if (server) {
+			await server.stop();
+			server = null;
+		}
+		await safeCleanup(TEST_DIR);
+	});
+
+	it("rejects conversion without file", async () => {
+		const formData = new FormData();
+		const res = await fetchWithTimeout("/api/docx/convert", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(400);
+		const data = await res.json();
+		expect(data.error).toBe("No file provided");
+	});
+
+	it("rejects non-docx files", async () => {
+		const formData = new FormData();
+		formData.append("file", new Blob(["not a docx"], { type: "text/plain" }), "readme.txt");
+		const res = await fetchWithTimeout("/api/docx/convert", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(400);
+		const data = await res.json();
+		expect(data.error).toBe("Only .docx files are supported");
+	});
+
+	it("converts a simple docx to markdown", async () => {
+		const docxPath = join(import.meta.dir, "../../node_modules/mammoth/test/test-data/single-paragraph.docx");
+		const buffer = await Bun.file(docxPath).arrayBuffer();
+
+		const formData = new FormData();
+		formData.append(
+			"file",
+			new Blob([buffer], { type: "application/vnd.openxmlformats-officedocument.wordprocessingml.document" }),
+			"test.docx",
+		);
+
+		const res = await fetchWithTimeout("/api/docx/convert", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(200);
+		const data = await res.json();
+		expect(typeof data.html).toBe("string");
+		expect(data.html.length).toBeGreaterThan(0);
+		expect(Array.isArray(data.images)).toBe(true);
+		expect(Array.isArray(data.messages)).toBe(true);
+	});
+
+	it("extracts images from docx and saves to temp directory", async () => {
+		const docxPath = join(import.meta.dir, "../../node_modules/mammoth/test/test-data/tiny-picture.docx");
+		const buffer = await Bun.file(docxPath).arrayBuffer();
+
+		const formData = new FormData();
+		formData.append(
+			"file",
+			new Blob([buffer], { type: "application/vnd.openxmlformats-officedocument.wordprocessingml.document" }),
+			"image.docx",
+		);
+
+		const res = await fetchWithTimeout("/api/docx/convert", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(200);
+		const data = await res.json();
+		expect(data.images.length).toBeGreaterThan(0);
+
+		const tempUrl = data.images[0].tempUrl;
+		expect(tempUrl).toMatch(/^\/assets\/\.temp\/[\w-]+\.png$/);
+
+		// Verify file exists on disk
+		const backlogRoot = dirname(filesystem.docsDir);
+		const assetsDir = join(backlogRoot, "assets");
+		const tempFile = join(assetsDir, ".temp", tempUrl.replace("/assets/.temp/", ""));
+		expect(await Bun.file(tempFile).exists()).toBe(true);
+	});
+});
diff --git a/src/test/server-upload-promote.test.ts b/src/test/server-upload-promote.test.ts
new file mode 100644
index 000000000..c92c80b61
--- /dev/null
+++ b/src/test/server-upload-promote.test.ts
@@ -0,0 +1,245 @@
+import { afterEach, beforeEach, describe, expect, it } from "bun:test";
+import { utimes } from "node:fs/promises";
+import { dirname, join } from "node:path";
+import { FileSystem } from "../file-system/operations.ts";
+import { BacklogServer } from "../server/index.ts";
+import { createUniqueTestDir, retry, safeCleanup } from "./test-utils.ts";
+
+let TEST_DIR: string;
+let filesystem: FileSystem;
+let server: BacklogServer | null = null;
+let serverPort = 0;
+
+async function fetchWithTimeout(path: string, options: RequestInit = {}, timeoutMs = 1000): Promise<Response> {
+	const controller = new AbortController();
+	const timeout = setTimeout(() => controller.abort(), timeoutMs);
+	try {
+		return await fetch(`http://127.0.0.1:${serverPort}${path}`, { ...options, signal: controller.signal });
+	} finally {
+		clearTimeout(timeout);
+	}
+}
+
+describe("BacklogServer upload and promote", () => {
+	beforeEach(async () => {
+		TEST_DIR = createUniqueTestDir("server-upload");
+		filesystem = new FileSystem(TEST_DIR);
+		await filesystem.ensureBacklogStructure();
+
+		await filesystem.saveConfig({
+			projectName: "Upload Test",
+			statuses: ["To Do", "In Progress", "Done"],
+			labels: [],
+			milestones: [],
+			dateFormat: "YYYY-MM-DD",
+			remoteOperations: false,
+		});
+
+		server = new BacklogServer(TEST_DIR);
+		await server.start(0, false);
+		const port = server.getPort();
+		expect(port).not.toBeNull();
+		serverPort = port ?? 0;
+
+		await retry(
+			async () => {
+				const res = await fetchWithTimeout("/api/status", {}, 500);
+				if (!res.ok) throw new Error("server not ready");
+				return true;
+			},
+			10,
+			50,
+		);
+	});
+
+	afterEach(async () => {
+		if (server) {
+			await server.stop();
+			server = null;
+		}
+		await safeCleanup(TEST_DIR);
+	});
+
+	it("uploads a file via multipart/form-data to temp directory", async () => {
+		const formData = new FormData();
+		formData.append("file", new Blob(["fake-png-data"], { type: "image/png" }), "screenshot.png");
+
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(200);
+		const data = await res.json();
+		expect(data.url).toMatch(/^\/assets\/\.temp\/[\w-]+\.png$/);
+
+		// Verify file exists on disk
+		const backlogRoot = dirname(filesystem.docsDir);
+		const assetsDir = join(backlogRoot, "assets");
+		const tempFile = join(assetsDir, ".temp", data.url.replace("/assets/.temp/", ""));
+		const file = Bun.file(tempFile);
+		expect(await file.exists()).toBe(true);
+		expect(await file.text()).toBe("fake-png-data");
+	});
+
+	it("uploads a file via JSON dataUri to temp directory", async () => {
+		const base64 = btoa("hello-image");
+		const dataUri = `data:image/png;base64,${base64}`;
+
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ dataUri }),
+		});
+		expect(res.status).toBe(200);
+		const data = await res.json();
+		expect(data.url).toMatch(/^\/assets\/\.temp\/[\w-]+\.png$/);
+
+		const backlogRoot = dirname(filesystem.docsDir);
+		const assetsDir = join(backlogRoot, "assets");
+		const tempFile = join(assetsDir, ".temp", data.url.replace("/assets/.temp/", ""));
+		const file = Bun.file(tempFile);
+		expect(await file.exists()).toBe(true);
+	});
+
+	it("rejects upload without file", async () => {
+		const formData = new FormData();
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			body: formData,
+		});
+		expect(res.status).toBe(400);
+		const data = await res.json();
+		expect(data.error).toBe("No file provided");
+	});
+
+	it("rejects upload with unsupported content type", async () => {
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			headers: { "Content-Type": "text/plain" },
+			body: "hello",
+		});
+		expect(res.status).toBe(400);
+	});
+
+	it("promotes temp assets to paste directory", async () => {
+		// Upload a temp file first
+		const formData = new FormData();
+		formData.append("file", new Blob(["promote-me"], { type: "image/png" }), "test.png");
+		const uploadRes = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			body: formData,
+		});
+		const uploadData = await uploadRes.json();
+		const tempUrl = uploadData.url;
+
+		// Promote it
+		const promoteRes = await fetchWithTimeout("/api/assets/promote", {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ urls: [tempUrl] }),
+		});
+		expect(promoteRes.status).toBe(200);
+		const promoteData = await promoteRes.json();
+		expect(promoteData[tempUrl]).toMatch(/^\/assets\/paste\/[\w-]+\.png$/);
+
+		// Verify temp file is gone and paste file exists
+		const backlogRoot = dirname(filesystem.docsDir);
+		const assetsDir = join(backlogRoot, "assets");
+		const tempPath = join(assetsDir, ".temp", tempUrl.replace("/assets/.temp/", ""));
+		const pastePath = join(assetsDir, "paste", promoteData[tempUrl].replace("/assets/paste/", ""));
+
+		expect(await Bun.file(tempPath).exists()).toBe(false);
+		expect(await Bun.file(pastePath).exists()).toBe(true);
+		expect(await Bun.file(pastePath).text()).toBe("promote-me");
+	});
+
+	it("ignores invalid URLs during promote", async () => {
+		const res = await fetchWithTimeout("/api/assets/promote", {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ urls: ["/assets/paste/already-promoted.png", "/assets/../escape.png"] }),
+		});
+		expect(res.status).toBe(200);
+		const data = await res.json();
+		expect(Object.keys(data)).toHaveLength(0);
+	});
+
+	it("blocks download from localhost", async () => {
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ url: "http://localhost:8080/image.png" }),
+		});
+		expect(res.status).toBe(400);
+		const data = await res.json();
+		expect(data.error).toBe("Failed to download image");
+	});
+
+	it("blocks download from private IP", async () => {
+		const res = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ url: "http://192.168.1.1/image.png" }),
+		});
+		expect(res.status).toBe(400);
+		const data = await res.json();
+		expect(data.error).toBe("Failed to download image");
+	});
+
+	it("cleans up temp assets older than 30 min on server start", async () => {
+		// Upload two temp files
+		const formData1 = new FormData();
+		formData1.append("file", new Blob(["old"], { type: "image/png" }), "old.png");
+		const uploadRes1 = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			body: formData1,
+		});
+		const uploadData1 = await uploadRes1.json();
+		const oldUrl = uploadData1.url;
+
+		const formData2 = new FormData();
+		formData2.append("file", new Blob(["fresh"], { type: "image/png" }), "fresh.png");
+		const uploadRes2 = await fetchWithTimeout("/api/upload?temp=1", {
+			method: "POST",
+			body: formData2,
+		});
+		const uploadData2 = await uploadRes2.json();
+		const freshUrl = uploadData2.url;
+
+		const backlogRoot = dirname(filesystem.docsDir);
+		const assetsDir = join(backlogRoot, "assets");
+		const oldPath = join(assetsDir, ".temp", oldUrl.replace("/assets/.temp/", ""));
+		const freshPath = join(assetsDir, ".temp", freshUrl.replace("/assets/.temp/", ""));
+
+		// Age the first file to 31 minutes ago
+		const agedTime = new Date(Date.now() - 31 * 60 * 1000);
+		await utimes(oldPath, agedTime, agedTime);
+
+		// Stop and restart the server
+		if (server) {
+			await server.stop();
+			server = null;
+		}
+		server = new BacklogServer(TEST_DIR);
+		await server.start(0, false);
+		const port = server.getPort();
+		expect(port).not.toBeNull();
+		serverPort = port ?? 0;
+
+		await retry(
+			async () => {
+				const res = await fetchWithTimeout("/api/status", {}, 500);
+				if (!res.ok) throw new Error("server not ready");
+				return true;
+			},
+			10,
+			50,
+		);
+
+		// Give cleanup a moment to run (it's async)
+		await new Promise((resolve) => setTimeout(resolve, 200));
+
+		expect(await Bun.file(oldPath).exists()).toBe(false);
+		expect(await Bun.file(freshPath).exists()).toBe(true);
+	});
+});
diff --git a/src/types/turndown-plugin-gfm.d.ts b/src/types/turndown-plugin-gfm.d.ts
new file mode 100644
index 000000000..f58eb5ee0
--- /dev/null
+++ b/src/types/turndown-plugin-gfm.d.ts
@@ -0,0 +1,8 @@
+declare module "turndown-plugin-gfm" {
+	import type TurndownService from "turndown";
+
+	export const gfm: (turndownService: TurndownService) => void;
+	export const tables: (turndownService: TurndownService) => void;
+	export const strikethrough: (turndownService: TurndownService) => void;
+	export const taskListItems: (turndownService: TurndownService) => void;
+}
diff --git a/src/types/turndown.d.ts b/src/types/turndown.d.ts
new file mode 100644
index 000000000..68e21d200
--- /dev/null
+++ b/src/types/turndown.d.ts
@@ -0,0 +1,28 @@
+declare module "turndown" {
+	interface Rule {
+		filter: string | string[] | ((node: HTMLElement) => boolean);
+		replacement: (content: string, node: HTMLElement, options: TurndownOptions) => string | null | undefined;
+	}
+
+	interface TurndownOptions {
+		headingStyle?: "setext" | "atx";
+		hr?: "***" | "---" | "___" | string;
+		bulletListMarker?: "*" | "+" | "-";
+		codeBlockStyle?: "indented" | "fenced";
+		fence?: "```" | "~~~" | string;
+		emDelimiter?: "_" | "*";
+		strongDelimiter?: "**" | "__";
+		linkStyle?: "inlined" | "referenced";
+		linkReferenceStyle?: "full" | "collapsed" | "shortcut";
+		preformattedCode?: boolean;
+	}
+
+	export default class TurndownService {
+		constructor(options?: TurndownOptions);
+		addRule(key: string, rule: Rule): this;
+		remove(keys: string | string[]): this;
+		use(plugin: (turndownService: TurndownService) => void): this;
+		escape(str: string): string;
+		turndown(html: string | Node): string;
+	}
+}
diff --git a/src/web/components/DocumentationDetail.tsx b/src/web/components/DocumentationDetail.tsx
index efa21700e..5fb06c5b2 100644
--- a/src/web/components/DocumentationDetail.tsx
+++ b/src/web/components/DocumentationDetail.tsx
@@ -1,7 +1,7 @@
 import {useState, useEffect, memo, useCallback} from 'react';
 import {useParams, useNavigate, useSearchParams} from 'react-router-dom';
 import {apiClient} from '../lib/api';
-import MDEditor from '@uiw/react-md-editor';
+import { PasteAwareMDEditor } from './PasteAwareMDEditor';
 import MermaidMarkdown from './MermaidMarkdown';
 import {type Document} from '../../types';
 import ErrorBoundary from '../components/ErrorBoundary';
@@ -36,7 +36,7 @@ const MarkdownEditor = memo(function MarkdownEditor({
     return (
         <div className="h-full w-full flex flex-col">
             <div className="flex-1 border border-gray-200 dark:border-gray-700 rounded-lg overflow-hidden bg-white dark:bg-gray-800">
-                <MDEditor
+                <PasteAwareMDEditor
                     value={value}
                     onChange={onChange}
                     preview="edit"
@@ -166,6 +166,19 @@ export default function DocumentationDetail({docs, onRefreshData}: Documentation
         }
     }, [id, docs]);
 
+    const extractTempImageUrls = (text: string): string[] => {
+        const matches = text.match(/\/assets\/\.temp\/[^)\s\\"']+/g);
+        return matches ? [...new Set(matches)] : [];
+    };
+
+    const replaceTempImageUrls = (text: string, mapping: Record<string, string>): string => {
+        let result = text;
+        for (const [oldUrl, newUrl] of Object.entries(mapping)) {
+            result = result.replaceAll(oldUrl, newUrl);
+        }
+        return result;
+    };
+
     const handleSave = useCallback(async () => {
         if (!docTitle.trim()) {
             setSaveError(new Error('Document title is required'));
@@ -178,9 +191,18 @@ export default function DocumentationDetail({docs, onRefreshData}: Documentation
             const normalizedTitle = docTitle.trim();
             const normalizedPath = docPath.trim();
 
+            // Promote temporary pasted images before saving.
+            let saveContent = content;
+            const tempUrls = extractTempImageUrls(content);
+            if (tempUrls.length > 0) {
+                const mapping = await apiClient.promoteAssets(tempUrls);
+                saveContent = replaceTempImageUrls(saveContent, mapping);
+                setContent(saveContent);
+            }
+
             if (isNewDocument) {
                 // Create new document
-                const result = await apiClient.createDoc(normalizedTitle, content, normalizedPath);
+                const result = await apiClient.createDoc(normalizedTitle, saveContent, normalizedPath);
                 // Refresh data and navigate to the new document
                 await onRefreshData();
                 // Show success toast
@@ -207,7 +229,7 @@ export default function DocumentationDetail({docs, onRefreshData}: Documentation
                 // Pass title only if it has changed
                 const updatedDocument = await apiClient.updateDoc(
                     addDocPrefix(id),
-                    content,
+                    saveContent,
                     titleChanged ? normalizedTitle : undefined,
                     pathChanged ? normalizedPath : undefined
                 );
diff --git a/src/web/components/FilePreviewModal.tsx b/src/web/components/FilePreviewModal.tsx
new file mode 100644
index 000000000..7117ddbf5
--- /dev/null
+++ b/src/web/components/FilePreviewModal.tsx
@@ -0,0 +1,171 @@
+import React, { useEffect, useState } from "react";
+import Modal from "./Modal";
+import { apiClient } from "../lib/api";
+import MermaidMarkdown from "./MermaidMarkdown";
+import { useTheme } from "../contexts/ThemeContext";
+
+interface Props {
+	path: string;
+	onClose: () => void;
+}
+
+const LANG_MAP: Record<string, string> = {
+	ts: "typescript",
+	tsx: "tsx",
+	js: "javascript",
+	jsx: "jsx",
+	py: "python",
+	json: "json",
+	yaml: "yaml",
+	yml: "yaml",
+	css: "css",
+	scss: "scss",
+	html: "html",
+	xml: "xml",
+	sh: "bash",
+	bash: "bash",
+	zsh: "zsh",
+	go: "go",
+	rs: "rust",
+	java: "java",
+	cpp: "cpp",
+	c: "c",
+	cs: "csharp",
+	php: "php",
+	rb: "ruby",
+	sql: "sql",
+	dockerfile: "dockerfile",
+	md: "markdown",
+};
+
+function getLanguage(filePath: string): string {
+	const ext = filePath.split(".").pop()?.toLowerCase() || "";
+	return LANG_MAP[ext] || ext;
+}
+
+function wrapInCodeBlock(content: string, language: string): string {
+	// Use longer fence if content contains triple backticks to avoid premature closing
+	const hasCodeFence = /\n```/.test(content);
+	const fence = hasCodeFence ? "````" : "```";
+	return `${fence}${language}\n${content}\n${fence}`;
+}
+
+export const FilePreviewModal: React.FC<Props> = ({ path, onClose }) => {
+	const { theme } = useTheme();
+	const [content, setContent] = useState<string>("");
+	const [filePath, setFilePath] = useState<string>("");
+	const [lineStart, setLineStart] = useState<number | undefined>();
+	const [lineEnd, setLineEnd] = useState<number | undefined>();
+	const [totalLines, setTotalLines] = useState<number>(0);
+	const [isMarkdown, setIsMarkdown] = useState<boolean>(false);
+	const [loading, setLoading] = useState(true);
+	const [error, setError] = useState<string | null>(null);
+
+	useEffect(() => {
+		let cancelled = false;
+
+		async function load() {
+			setLoading(true);
+			setError(null);
+			try {
+				const data = await apiClient.fetchFileContent(path);
+				if (cancelled) return;
+				setContent(data.content);
+				setFilePath(data.path);
+				setLineStart(data.lineStart);
+				setLineEnd(data.lineEnd);
+				setTotalLines(data.totalLines);
+				setIsMarkdown(data.isMarkdown);
+			} catch (err) {
+				if (cancelled) return;
+				const message = err instanceof Error ? err.message : "Failed to load file";
+				setError(message);
+			} finally {
+				if (!cancelled) setLoading(false);
+			}
+		}
+
+		void load();
+		return () => {
+			cancelled = true;
+		};
+	}, [path]);
+
+	const titleParts = [filePath || path];
+	if (lineStart !== undefined && lineEnd !== undefined) {
+		titleParts.push(`(lines ${lineStart}-${lineEnd})`);
+	} else if (lineStart !== undefined) {
+		titleParts.push(`(line ${lineStart})`);
+	}
+	const title = titleParts.join(" ");
+
+	const isPartial = lineStart !== undefined && lineEnd !== undefined;
+	const startLineNumber = (lineStart ?? 1) - 1;
+
+	return (
+		<Modal isOpen onClose={onClose} title={title} maxWidthClass="max-w-4xl">
+			{loading && <div className="text-sm text-gray-500 dark:text-gray-400">Loading...</div>}
+			{error && <div className="text-sm text-red-600 dark:text-red-400">{error}</div>}
+			{!loading && !error && (
+				<div className="space-y-2">
+					<div className="text-xs text-gray-500 dark:text-gray-400">
+						{totalLines} line{totalLines !== 1 ? "s" : ""} total
+						{isPartial && (
+							<span className="ml-2 text-blue-600 dark:text-blue-400">
+								showing lines {lineStart}-{lineEnd}
+							</span>
+						)}
+					</div>
+					{isMarkdown ? (
+						<div
+							className="prose prose-sm !max-w-none wmde-markdown rounded-lg border border-gray-200 dark:border-gray-700 p-4 bg-white dark:bg-gray-800"
+							data-color-mode={theme}
+						>
+							<MermaidMarkdown source={content} />
+						</div>
+					) : (
+						<div className="rounded-lg border border-gray-200 dark:border-gray-700 max-h-[60vh] overflow-auto">
+							{isPartial && (
+								<div className="bg-blue-50 dark:bg-blue-900/20 text-blue-700 dark:text-blue-300 text-xs px-4 py-1.5 border-b border-blue-200 dark:border-blue-800 sticky top-0 z-10">
+									Lines {lineStart}-{lineEnd} of {totalLines}
+								</div>
+							)}
+							<div
+								className="code-file-preview"
+								style={{ counterReset: `line ${startLineNumber}` }}
+							>
+								<MermaidMarkdown source={wrapInCodeBlock(content, getLanguage(filePath))} />
+							</div>
+						</div>
+					)}
+				</div>
+			)}
+			<style>{`
+				.code-file-preview .code-line {
+					display: block;
+					counter-increment: line;
+					padding-left: 0.5rem;
+				}
+				.code-file-preview .code-line::before {
+					content: counter(line);
+					display: inline-block;
+					width: 2.5em;
+					margin-right: 1em;
+					text-align: right;
+					color: #6b7280;
+					user-select: none;
+					flex-shrink: 0;
+				}
+				.dark .code-file-preview .code-line::before {
+					color: #9ca3af;
+				}
+				.code-file-preview pre {
+					margin: 0 !important;
+					border-radius: 0 !important;
+				}
+			`}</style>
+		</Modal>
+	);
+};
+
+export default FilePreviewModal;
diff --git a/src/web/components/MermaidMarkdown.tsx b/src/web/components/MermaidMarkdown.tsx
index 106b56fdd..bf5ac4149 100644
--- a/src/web/components/MermaidMarkdown.tsx
+++ b/src/web/components/MermaidMarkdown.tsx
@@ -1,16 +1,36 @@
-import { useEffect, useRef } from "react";
+import React, { useEffect, useRef } from "react";
 import MDEditor from "@uiw/react-md-editor";
 import { renderMermaidIn } from "../utils/mermaid";
+import { apiClient } from "../lib/api";
 
 interface Props {
 	source: string;
+	onFileClick?: (path: string) => void;
 }
 
 const URI_AUTOLINK_PREFIX_REGEX = /^<[A-Za-z][A-Za-z0-9+.-]{1,31}:[^<>\u0000-\u0020]*>/;
 const EMAIL_AUTOLINK_PREFIX_REGEX = /^<[A-Za-z0-9.!#$%&'*+/=?^_`{|}~-]+@[A-Za-z0-9.-]+\.[A-Za-z0-9-]+>/;
 
 function sanitizeMarkdownSource(source: string): string {
+	const protectedRanges: { start: number; end: number }[] = [];
+
+	// Protect code blocks (```...```)
+	for (const match of source.matchAll(/```[\s\S]*?```/g)) {
+		protectedRanges.push({ start: match.index!, end: match.index! + match[0].length });
+	}
+
+	// Protect inline code (`...`)
+	for (const match of source.matchAll(/`[^`\n]+`/g)) {
+		protectedRanges.push({ start: match.index!, end: match.index! + match[0].length });
+	}
+
 	return source.replace(/<(?=[A-Za-z])/g, (match, offset, fullText) => {
+		// Skip replacement inside code blocks and inline code
+		for (const range of protectedRanges) {
+			if (offset >= range.start && offset < range.end) {
+				return match;
+			}
+		}
 		const remaining = fullText.slice(offset);
 		if (URI_AUTOLINK_PREFIX_REGEX.test(remaining) || EMAIL_AUTOLINK_PREFIX_REGEX.test(remaining)) {
 			return match;
@@ -19,7 +39,14 @@ function sanitizeMarkdownSource(source: string): string {
 	});
 }
 
-export default function MermaidMarkdown({ source }: Props) {
+function isExternalLink(href?: string): boolean {
+	if (!href) return true;
+	if (href.startsWith("#")) return false;
+	if (/^[a-z][a-z0-9+.-]*:/i.test(href)) return true;
+	return false;
+}
+
+export default function MermaidMarkdown({ source, onFileClick }: Props) {
 	const ref = useRef<HTMLDivElement | null>(null);
 	const safeSource = sanitizeMarkdownSource(source);
 
@@ -37,9 +64,50 @@ export default function MermaidMarkdown({ source }: Props) {
 		return () => cancelAnimationFrame(frameId);
 	}, [safeSource]);
 
+	const LinkComponent = React.useCallback(
+		({ href, children }: { href?: string; children?: React.ReactNode }) => {
+			if (isExternalLink(href)) {
+				return (
+					<a href={href} target="_blank" rel="noopener noreferrer">
+						{children}
+					</a>
+				);
+			}
+
+			if (!onFileClick) {
+				return <a href={href}>{children}</a>;
+			}
+
+			const handleClick = async (e: React.MouseEvent) => {
+				e.preventDefault();
+				if (!href) return;
+				try {
+					// Verify file exists before opening preview
+					await apiClient.fetchFileContent(href);
+					onFileClick(href);
+				} catch {
+					// File not found or inaccessible: fall back to normal link behavior
+					window.open(href, "_blank");
+				}
+			};
+
+			return (
+				<a
+					href={href}
+					onClick={handleClick}
+					className="text-blue-600 dark:text-blue-400 hover:underline cursor-pointer"
+					title="Click to preview file"
+				>
+					{children}
+				</a>
+			);
+		},
+		[onFileClick],
+	);
+
 	return (
 		<div ref={ref} className="wmde-markdown">
-			<MDEditor.Markdown source={safeSource} />
+			<MDEditor.Markdown source={safeSource} components={{ a: LinkComponent }} />
 		</div>
 	);
 }
diff --git a/src/web/components/PasteAwareMDEditor.tsx b/src/web/components/PasteAwareMDEditor.tsx
new file mode 100644
index 000000000..e33eeaab5
--- /dev/null
+++ b/src/web/components/PasteAwareMDEditor.tsx
@@ -0,0 +1,275 @@
+import React, { useCallback, useRef, useState } from "react";
+import MDEditor, { commands } from "@uiw/react-md-editor";
+import TurndownService from "turndown";
+import { gfm } from "turndown-plugin-gfm";
+import { apiClient } from "../lib/api";
+import { cleanHtml, handlePasteAsMarkdown } from "../utils/paste-as-markdown";
+
+type MDEditorProps = React.ComponentProps<typeof MDEditor>;
+
+async function uploadImage(source: Blob | string): Promise<string | null> {
+	try {
+		if (typeof source === "string") {
+			if (source.startsWith("data:")) {
+				const result = await apiClient.uploadTempAssetFromDataUri(source);
+				return result.url;
+			}
+			const result = await apiClient.uploadTempAssetFromUrl(source);
+			return result.url;
+		}
+		const file = new File([source], "image.png", { type: source.type || "image/png" });
+		const result = await apiClient.uploadTempAsset(file);
+		return result.url;
+	} catch (err) {
+		console.error("Image upload failed:", err);
+		return null;
+	}
+}
+
+function getImageFileFromClipboard(data: DataTransfer): File | null {
+	// Some browsers/OS put the screenshot in clipboardData.files.
+	for (const file of data.files) {
+		if (file.type.startsWith("image/")) {
+			return file;
+		}
+	}
+	// Others expose it through DataTransferItemList.
+	for (const item of data.items) {
+		if (item.kind === "file" && item.type.startsWith("image/")) {
+			const file = item.getAsFile();
+			if (file) return file;
+		}
+	}
+	return null;
+}
+
+function insertMarkdownAtCaret(
+	textarea: HTMLTextAreaElement,
+	markdown: string,
+	onChange: (value: string) => void,
+): void {
+	const start = textarea.selectionStart;
+	const end = textarea.selectionEnd;
+	const currentValue = textarea.value;
+	const newValue = currentValue.slice(0, start) + markdown + currentValue.slice(end);
+	onChange(newValue);
+	requestAnimationFrame(() => {
+		textarea.selectionStart = textarea.selectionEnd = start + markdown.length;
+		textarea.focus();
+	});
+}
+
+export const PasteAwareMDEditor: React.FC<MDEditorProps> = ({
+	value,
+	onChange,
+	textareaProps,
+	extraCommands: propExtraCommands,
+	...rest
+}) => {
+	const textareaRef = useRef<HTMLTextAreaElement | null>(null);
+	const fileInputRef = useRef<HTMLInputElement | null>(null);
+	const [isConverting, setIsConverting] = useState(false);
+
+	const handleDocxUpload = useCallback(
+		async (file: File) => {
+			if (!onChange) return;
+			setIsConverting(true);
+			try {
+				const result = await apiClient.convertDocx(file);
+				const cleanedHtml = await cleanHtml(result.html, { keepMedia: true });
+
+				const turndownService = new TurndownService({
+					headingStyle: "atx",
+					bulletListMarker: "-",
+					codeBlockStyle: "fenced",
+					strongDelimiter: "**",
+					emDelimiter: "*",
+					fence: "```",
+				});
+				turndownService.use(gfm);
+				turndownService.remove(["style", "meta", "link", "script"]);
+				turndownService.addRule("keepBr", {
+					filter: "br",
+					replacement: () => "<br>",
+				});
+
+				let markdown = turndownService.turndown(cleanedHtml);
+
+				// Post-processing: move whitespace inside bold/italic markers to the outside.
+				let prev: string;
+				do {
+					prev = markdown;
+					markdown = markdown.replace(/\*\*(\s*)([^\n]*?)(\s*)\*\*/g, "$1**$2**$3");
+				} while (markdown !== prev);
+
+				do {
+					prev = markdown;
+					markdown = markdown.replace(/(?<!\*)\*(\s*)([^\s*][^\n]*?[^\s*])(\s*)\*(?!\*)/g, "$1*$2*$3");
+				} while (markdown !== prev);
+
+				// Ensure a space after bold/italic closers when they touch plain text.
+				markdown = markdown.replace(/\*\*([^\s][^\n]*?)\*\*([^\s*<|\n\r])/g, "**$1** $2");
+				markdown = markdown.replace(/(?<!\*)\*([^\s*][^\n]*?)\*([^\s*<|\n\r])(?!\*)/g, "*$1* $2");
+
+				// Ensure ordered-list markers are followed by a space.
+				markdown = markdown.replace(/(^|\s)(\d+\.)([^\s\d])/g, "$1$2 $3");
+
+				const textarea =
+					textareaRef.current ??
+					document.querySelector<HTMLTextAreaElement>(".w-md-editor-text-input");
+				if (textarea) {
+					insertMarkdownAtCaret(textarea, markdown, onChange);
+				}
+				if (result.messages.length > 0) {
+					console.warn("DOCX conversion messages:", result.messages);
+				}
+			} catch (err) {
+				console.error("Word upload failed:", err);
+				alert(err instanceof Error ? err.message : "Failed to convert Word document");
+			} finally {
+				setIsConverting(false);
+			}
+		},
+		[onChange],
+	);
+
+	const handlePaste = useCallback(
+		async (e: React.ClipboardEvent<HTMLTextAreaElement>) => {
+			if (!onChange) {
+				textareaProps?.onPaste?.(e);
+				return;
+			}
+
+			const html = e.clipboardData.getData("text/html");
+			const imageFile = getImageFileFromClipboard(e.clipboardData);
+			const textarea = e.currentTarget;
+
+			// Pure image paste (screenshot tools) — no HTML, just an image blob.
+			if (imageFile && !html) {
+				e.preventDefault();
+				const url = await uploadImage(imageFile);
+				if (url) {
+					insertMarkdownAtCaret(textarea, `![image](${url})`, onChange);
+				}
+				return;
+			}
+
+			// Rich-text paste (Word, web pages, Excel) — may contain <img> tags.
+			const markdown = await handlePasteAsMarkdown(e, uploadImage);
+			if (markdown !== null) {
+				e.preventDefault();
+				let combined = markdown;
+				// Excel places both HTML (table) and an image blob on the clipboard.
+				if (imageFile) {
+					const url = await uploadImage(imageFile);
+					if (url) {
+						combined += `\n\n![image](${url})`;
+					}
+				}
+				insertMarkdownAtCaret(textarea, combined, onChange);
+				return;
+			}
+
+			// Screenshot tools sometimes place both a bare <img> (invalid src) and the
+			// actual image blob on the clipboard. If the HTML path couldn't handle the
+			// paste but a binary image is present, fall back to direct image upload.
+			if (imageFile) {
+				e.preventDefault();
+				const url = await uploadImage(imageFile);
+				if (url) {
+					insertMarkdownAtCaret(textarea, `![image](${url})`, onChange);
+				}
+				return;
+			}
+
+			if (textareaProps?.onPaste) {
+				textareaProps.onPaste(e);
+			}
+		},
+		[onChange, textareaProps],
+	);
+
+	const wordCommand: commands.ICommand = {
+		name: "upload-word",
+		keyCommand: "upload-word",
+		render: () => {
+			return (
+				<button
+					type="button"
+					disabled={isConverting}
+					title="Upload Word document (.docx)"
+					onMouseDown={(e) => e.preventDefault()}
+					onClick={() => fileInputRef.current?.click()}
+				>
+					{isConverting ? (
+						<span className="inline-block h-3 w-3 animate-spin rounded-full border-2 border-gray-300 border-t-blue-500" />
+					) : (
+						<svg className="h-3.5 w-3.5" viewBox="0 0 1024 1024" xmlns="http://www.w3.org/2000/svg">
+							<path
+								d="M106.915276 0.008063C87.725354 0.008063 68.535433 19.189921 68.535433 38.379843V985.088c0 19.189921 19.189921 38.379843 38.379843 38.379843h805.976693c19.189921 0 38.379843-19.189921 38.379842-38.379843V223.893165L727.394772 0.008063H106.915276z"
+								fill="#2C97FF"
+							/>
+							<path
+								d="M727.394772 0.008063v184.223244c0 19.189921 19.189921 39.661858 39.661858 39.661858H951.271811L727.394772 0.008063z"
+								fill="#99D3FF"
+							/>
+							<path
+								d="M738.900661 329.881197c-21.600756 0-39.847307 18.246551-39.847307 39.847307v256.056441L538.583685 457.977953c-7.071244-8.482268-16.988724-12.965291-28.680063-12.965292-11.038236 0-22.011969 4.966803-28.494614 12.739528L318.197921 627.123402V369.728504c0-21.608819-18.254614-39.847307-39.85537-39.847307s-39.85537 18.246551-39.85537 39.847307v356.940598c0 16.311433 10.56252 31.550488 25.688693 37.049449a41.064819 41.064819 0 0 0 14.053795 2.467276c10.965669 0 21.802331-4.33789 29.889512-12.425071l201.792504-210.62148L711.502614 752.277165c7.071244 8.466142 16.988724 12.965291 28.680063 12.965292 5.418331 0 10.167433-0.120945 12.900788-1.531969 15.110047-5.490898 25.664504-20.729953 25.664504-37.041386v-356.948661c0-21.592693-18.246551-39.839244-39.847308-39.839244"
+								fill="#FFFFFF"
+							/>
+							</svg>
+						)}
+					</button>
+				);
+		},
+	};
+
+	return (
+		<div
+			className="relative"
+			onDragOver={(e) => e.preventDefault()}
+			onDrop={(e) => {
+				e.preventDefault();
+				const file = e.dataTransfer.files[0];
+				if (file && file.name.toLowerCase().endsWith(".docx")) {
+					void handleDocxUpload(file);
+				}
+			}}
+		>
+			{onChange && (
+				<input
+					ref={fileInputRef}
+					type="file"
+					accept=".docx"
+					className="sr-only"
+					onChange={(e) => {
+						const file = e.target.files?.[0];
+						if (file) void handleDocxUpload(file);
+						e.target.value = "";
+					}}
+				/>
+			)}
+			<MDEditor
+				{...rest}
+				value={value}
+				onChange={onChange}
+				extraCommands={[wordCommand, ...(propExtraCommands ?? commands.getExtraCommands())]}
+				textareaProps={{
+					...textareaProps,
+					// biome-ignore lint/suspicious/noExplicitAny: library types don't expose ref on textareaProps
+					ref: (el: HTMLTextAreaElement | null) => {
+						textareaRef.current = el;
+						const originalRef = (textareaProps as any)?.ref;
+						if (typeof originalRef === "function") {
+							originalRef(el);
+						} else if (originalRef && typeof originalRef === "object" && "current" in originalRef) {
+							(originalRef as React.MutableRefObject<HTMLTextAreaElement | null>).current = el;
+						}
+					},
+					onPaste: handlePaste,
+					// biome-ignore lint/suspicious/noExplicitAny: library types don't expose ref on textareaProps
+				} as any}
+			/>
+		</div>
+	);
+};
diff --git a/src/web/components/TaskDetailsModal.tsx b/src/web/components/TaskDetailsModal.tsx
index 45724ac80..2deb2d962 100644
--- a/src/web/components/TaskDetailsModal.tsx
+++ b/src/web/components/TaskDetailsModal.tsx
@@ -3,9 +3,10 @@ import type { AcceptanceCriterion, Milestone, Task } from "../../types";
 import Modal from "./Modal";
 import { apiClient } from "../lib/api";
 import { useTheme } from "../contexts/ThemeContext";
-import MDEditor from "@uiw/react-md-editor";
+import { PasteAwareMDEditor } from "./PasteAwareMDEditor";
 import AcceptanceCriteriaEditor from "./AcceptanceCriteriaEditor";
 import MermaidMarkdown from './MermaidMarkdown';
+import FilePreviewModal from "./FilePreviewModal";
 import ChipInput from "./ChipInput";
 import DependencyInput from "./DependencyInput";
 import { formatStoredUtcDateForDisplay } from "../utils/date-display";
@@ -227,6 +228,7 @@ export const TaskDetailsModal: React.FC<Props> = ({
   const [references, setReferences] = useState<string[]>(task?.references || []);
   const [milestone, setMilestone] = useState<string>(task?.milestone || "");
   const [availableTasks, setAvailableTasks] = useState<Task[]>([]);
+  const [previewFilePath, setPreviewFilePath] = useState<string | null>(null);
   const milestoneSelectionValue = resolveMilestoneToId(milestone);
   const hasMilestoneSelection = (milestoneEntities ?? []).some((milestoneEntity) => milestoneEntity.id === milestoneSelectionValue);
 
@@ -417,6 +419,19 @@ export const TaskDetailsModal: React.FC<Props> = ({
     return payload;
   };
 
+  const extractTempImageUrls = (text: string): string[] => {
+    const matches = text.match(/\/assets\/\.temp\/[^)\s\\"']+/g);
+    return matches ? [...new Set(matches)] : [];
+  };
+
+  const replaceTempImageUrls = (text: string, mapping: Record<string, string>): string => {
+    let result = text;
+    for (const [oldUrl, newUrl] of Object.entries(mapping)) {
+      result = result.replaceAll(oldUrl, newUrl);
+    }
+    return result;
+  };
+
   const handleSave = async () => {
     setSaving(true);
     setError(null);
@@ -429,12 +444,37 @@ export const TaskDetailsModal: React.FC<Props> = ({
     }
 
     try {
+      // Promote temporary pasted images before saving.
+      let saveDescription = description;
+      let savePlan = plan;
+      let saveNotes = notes;
+      let saveFinalSummary = finalSummary;
+
+      const tempUrls = [
+        ...extractTempImageUrls(description),
+        ...extractTempImageUrls(plan),
+        ...extractTempImageUrls(notes),
+        ...extractTempImageUrls(finalSummary),
+      ];
+      const uniqueTempUrls = [...new Set(tempUrls)];
+      if (uniqueTempUrls.length > 0) {
+        const mapping = await apiClient.promoteAssets(uniqueTempUrls);
+        saveDescription = replaceTempImageUrls(saveDescription, mapping);
+        savePlan = replaceTempImageUrls(savePlan, mapping);
+        saveNotes = replaceTempImageUrls(saveNotes, mapping);
+        saveFinalSummary = replaceTempImageUrls(saveFinalSummary, mapping);
+        setDescription(saveDescription);
+        setPlan(savePlan);
+        setNotes(saveNotes);
+        setFinalSummary(saveFinalSummary);
+      }
+
       const taskData: TaskUpdatePayload = {
         title: title.trim(),
-        description,
-        implementationPlan: plan,
-        implementationNotes: notes,
-        finalSummary,
+        description: saveDescription,
+        implementationPlan: savePlan,
+        implementationNotes: saveNotes,
+        finalSummary: saveFinalSummary,
         acceptanceCriteriaItems: criteria,
         status,
         assignee,
@@ -564,6 +604,7 @@ export const TaskDetailsModal: React.FC<Props> = ({
   const documentation = task?.documentation ?? [];
 
   return (
+    <>
     <Modal
       isOpen={isOpen}
       onClose={() => {
@@ -665,14 +706,14 @@ export const TaskDetailsModal: React.FC<Props> = ({
             {mode === "preview" ? (
               description ? (
                 <div className="prose prose-sm !max-w-none wmde-markdown" data-color-mode={theme}>
-                  <MermaidMarkdown source={description} />
+                  <MermaidMarkdown source={description} onFileClick={(path) => setPreviewFilePath(path)} />
                 </div>
               ) : (
                 <div className="text-sm text-gray-500 dark:text-gray-400">No description</div>
               )
             ) : (
               <div className="border border-gray-200 dark:border-gray-700 rounded-md">
-                <MDEditor
+                <PasteAwareMDEditor
                   value={description}
                   onChange={(val) => setDescription(val || "")}
                   preview="edit"
@@ -702,9 +743,13 @@ export const TaskDetailsModal: React.FC<Props> = ({
                             {ref}
                           </a>
                         ) : (
-                          <code className="text-sm font-mono text-gray-700 dark:text-gray-300 bg-gray-100 dark:bg-gray-700 px-2 py-0.5 rounded break-all">
+                          <button
+                            onClick={() => setPreviewFilePath(ref)}
+                            className="text-sm font-mono text-gray-700 dark:text-gray-300 bg-gray-100 dark:bg-gray-700 px-2 py-0.5 rounded break-all hover:bg-gray-200 dark:hover:bg-gray-600 transition-colors text-left"
+                            title="Click to preview"
+                          >
                             {ref}
-                          </code>
+                          </button>
                         )}
                       </span>
                       {!isFromOtherBranch && (
@@ -776,9 +821,13 @@ export const TaskDetailsModal: React.FC<Props> = ({
                             {doc}
                           </a>
                         ) : (
-                          <code className="text-sm font-mono text-gray-700 dark:text-gray-300 bg-gray-100 dark:bg-gray-700 px-2 py-0.5 rounded break-all">
+                          <button
+                            onClick={() => setPreviewFilePath(doc)}
+                            className="text-sm font-mono text-gray-700 dark:text-gray-300 bg-gray-100 dark:bg-gray-700 px-2 py-0.5 rounded break-all hover:bg-gray-200 dark:hover:bg-gray-600 transition-colors text-left"
+                            title="Click to preview"
+                          >
                             {doc}
-                          </code>
+                          </button>
                         )}
                       </span>
                     </li>
@@ -860,14 +909,14 @@ export const TaskDetailsModal: React.FC<Props> = ({
             {mode === "preview" ? (
               plan ? (
                 <div className="prose prose-sm !max-w-none wmde-markdown" data-color-mode={theme}>
-                  <MermaidMarkdown source={plan} />
+                  <MermaidMarkdown source={plan} onFileClick={(path) => setPreviewFilePath(path)} />
                 </div>
               ) : (
                 <div className="text-sm text-gray-500 dark:text-gray-400">No plan</div>
               )
             ) : (
               <div className="border border-gray-200 dark:border-gray-700 rounded-md">
-                <MDEditor
+                <PasteAwareMDEditor
                   value={plan}
                   onChange={(val) => setPlan(val || "")}
                   preview="edit"
@@ -884,14 +933,14 @@ export const TaskDetailsModal: React.FC<Props> = ({
             {mode === "preview" ? (
               notes ? (
                 <div className="prose prose-sm !max-w-none wmde-markdown" data-color-mode={theme}>
-                  <MermaidMarkdown source={notes} />
+                  <MermaidMarkdown source={notes} onFileClick={(path) => setPreviewFilePath(path)} />
                 </div>
               ) : (
                 <div className="text-sm text-gray-500 dark:text-gray-400">No notes</div>
               )
             ) : (
               <div className="border border-gray-200 dark:border-gray-700 rounded-md">
-                <MDEditor
+                <PasteAwareMDEditor
                   value={notes}
                   onChange={(val) => setNotes(val || "")}
                   preview="edit"
@@ -908,11 +957,11 @@ export const TaskDetailsModal: React.FC<Props> = ({
               <SectionHeader title="Final Summary" right="Completion summary" />
               {mode === "preview" ? (
                 <div className="prose prose-sm !max-w-none wmde-markdown" data-color-mode={theme}>
-                  <MermaidMarkdown source={finalSummary} />
+                  <MermaidMarkdown source={finalSummary} onFileClick={(path) => setPreviewFilePath(path)} />
                 </div>
               ) : (
                 <div className="border border-gray-200 dark:border-gray-700 rounded-md">
-                  <MDEditor
+                  <PasteAwareMDEditor
                     value={finalSummary}
                     onChange={(val) => setFinalSummary(val || "")}
                     preview="edit"
@@ -1068,6 +1117,13 @@ export const TaskDetailsModal: React.FC<Props> = ({
         </div>
       </div>
     </Modal>
+    {previewFilePath && (
+      <FilePreviewModal
+        path={previewFilePath}
+        onClose={() => setPreviewFilePath(null)}
+      />
+    )}
+    </>
   );
 };
 
diff --git a/src/web/lib/api.ts b/src/web/lib/api.ts
index 8f811a2eb..267ef45e9 100644
--- a/src/web/lib/api.ts
+++ b/src/web/lib/api.ts
@@ -533,6 +533,93 @@ export class ApiClient {
 		return this.fetchJson<InitializationStatus>(`${API_BASE}/status`);
 	}
 
+	async fetchFileContent(path: string): Promise<{
+		content: string;
+		path: string;
+		lineStart?: number;
+		lineEnd?: number;
+		totalLines: number;
+		isMarkdown: boolean;
+	}> {
+		return this.fetchJson<{
+			content: string;
+			path: string;
+			lineStart?: number;
+			lineEnd?: number;
+			totalLines: number;
+			isMarkdown: boolean;
+		}>(`${API_BASE}/file-content?path=${encodeURIComponent(path)}`);
+	}
+
+	async uploadTempAsset(file: File): Promise<{ url: string }> {
+		const formData = new FormData();
+		formData.append("file", file);
+		const response = await fetch(`${API_BASE}/upload?temp=1`, {
+			method: "POST",
+			body: formData,
+		});
+		if (!response.ok) {
+			const data = await response.json().catch(() => ({}));
+			throw new Error(data.error || "Failed to upload asset");
+		}
+		return response.json();
+	}
+
+	async uploadTempAssetFromUrl(imageUrl: string): Promise<{ url: string }> {
+		const response = await fetch(`${API_BASE}/upload?temp=1`, {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ url: imageUrl }),
+		});
+		if (!response.ok) {
+			const data = await response.json().catch(() => ({}));
+			throw new Error(data.error || "Failed to upload asset from URL");
+		}
+		return response.json();
+	}
+
+	async uploadTempAssetFromDataUri(dataUri: string): Promise<{ url: string }> {
+		const response = await fetch(`${API_BASE}/upload?temp=1`, {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ dataUri }),
+		});
+		if (!response.ok) {
+			const data = await response.json().catch(() => ({}));
+			throw new Error(data.error || "Failed to upload asset from data URI");
+		}
+		return response.json();
+	}
+
+	async convertDocx(
+		file: File,
+	): Promise<{ html: string; images: { tempUrl: string; alt: string }[]; messages: string[] }> {
+		const formData = new FormData();
+		formData.append("file", file);
+		const response = await fetch(`${API_BASE}/docx/convert`, {
+			method: "POST",
+			body: formData,
+		});
+		if (!response.ok) {
+			const data = await response.json().catch(() => ({}));
+			throw new Error(data.error || "Failed to convert Word document");
+		}
+		return response.json();
+	}
+
+	async promoteAssets(urls: string[]): Promise<Record<string, string>> {
+		const response = await fetch(`${API_BASE}/assets/promote`, {
+			method: "POST",
+			headers: { "Content-Type": "application/json" },
+			body: JSON.stringify({ urls }),
+		});
+		if (!response.ok) {
+			const data = await response.json().catch(() => ({}));
+			throw new Error(data.error || "Failed to promote assets");
+		}
+		return response.json();
+	}
+
 	async initializeProject(options: {
 		projectName: string;
 		backlogDirectory?: string;
diff --git a/src/web/styles/style.css b/src/web/styles/style.css
index 9a7648db1..c6eb41525 100644
--- a/src/web/styles/style.css
+++ b/src/web/styles/style.css
@@ -1,2 +1,2 @@
 /*! tailwindcss v4.2.2 | MIT License | https://tailwindcss.com */
-@layer properties{@supports (((-webkit-hyphens:none)) and (not (margin-trim:inline))) or ((-moz-orient:inline) and (not (color:rgb(from red r g b)))){*,:before,:after,::backdrop{--tw-translate-x:0;--tw-translate-y:0;--tw-translate-z:0;--tw-scale-x:1;--tw-scale-y:1;--tw-scale-z:1;--tw-rotate-x:initial;--tw-rotate-y:initial;--tw-rotate-z:initial;--tw-skew-x:initial;--tw-skew-y:initial;--tw-space-y-reverse:0;--tw-space-x-reverse:0;--tw-divide-y-reverse:0;--tw-border-style:solid;--tw-gradient-position:initial;--tw-gradient-from:#0000;--tw-gradient-via:#0000;--tw-gradient-to:#0000;--tw-gradient-stops:initial;--tw-gradient-via-stops:initial;--tw-gradient-from-position:0%;--tw-gradient-via-position:50%;--tw-gradient-to-position:100%;--tw-leading:initial;--tw-font-weight:initial;--tw-tracking:initial;--tw-ordinal:initial;--tw-slashed-zero:initial;--tw-numeric-figure:initial;--tw-numeric-spacing:initial;--tw-numeric-fraction:initial;--tw-shadow:0 0 #0000;--tw-shadow-color:initial;--tw-shadow-alpha:100%;--tw-inset-shadow:0 0 #0000;--tw-inset-shadow-color:initial;--tw-inset-shadow-alpha:100%;--tw-ring-color:initial;--tw-ring-shadow:0 0 #0000;--tw-inset-ring-color:initial;--tw-inset-ring-shadow:0 0 #0000;--tw-ring-inset:initial;--tw-ring-offset-width:0px;--tw-ring-offset-color:#fff;--tw-ring-offset-shadow:0 0 #0000;--tw-outline-style:solid;--tw-blur:initial;--tw-brightness:initial;--tw-contrast:initial;--tw-grayscale:initial;--tw-hue-rotate:initial;--tw-invert:initial;--tw-opacity:initial;--tw-saturate:initial;--tw-sepia:initial;--tw-drop-shadow:initial;--tw-drop-shadow-color:initial;--tw-drop-shadow-alpha:100%;--tw-drop-shadow-size:initial;--tw-backdrop-blur:initial;--tw-backdrop-brightness:initial;--tw-backdrop-contrast:initial;--tw-backdrop-grayscale:initial;--tw-backdrop-hue-rotate:initial;--tw-backdrop-invert:initial;--tw-backdrop-opacity:initial;--tw-backdrop-saturate:initial;--tw-backdrop-sepia:initial;--tw-duration:initial;--tw-content:""}}}@layer theme{:root,:host{--font-sans:ui-sans-serif, system-ui, sans-serif, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol", "Noto Color Emoji";--font-mono:ui-monospace, SFMono-Regular, Menlo, Monaco, Consolas, "Liberation Mono", "Courier New", monospace;--color-red-50:oklch(97.1% .013 17.38);--color-red-100:oklch(93.6% .032 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103.193);--color-yellow-200:oklch(94.5% .129 101.54);--color-yellow-300:oklch(90.5% .182 98.111);--color-yellow-400:oklch(85.2% .199 91.936);--color-yellow-500:oklch(79.5% .184 86.047);--color-yellow-700:oklch(55.4% .135 66.442);--color-yellow-800:oklch(47.6% .114 61.907);--color-yellow-900:oklch(42.1% .095 57.708);--color-green-50:oklch(98.2% .018 155.826);--color-green-100:oklch(96.2% .044 156.743);--color-green-200:oklch(92.5% .084 155.995);--color-green-300:oklch(87.1% .15 154.449);--color-green-400:oklch(79.2% .209 151.711);--color-green-500:oklch(72.3% .219 149.579);--color-green-600:oklch(62.7% .194 149.214);--color-green-700:oklch(52.7% .154 150.069);--color-green-800:oklch(44.8% .119 151.328);--color-green-900:oklch(39.3% .095 152.535);--color-emerald-100:oklch(95% .052 163.051);--color-emerald-300:oklch(84.5% .143 164.978);--color-emerald-400:oklch(76.5% .177 163.223);--color-emerald-500:oklch(69.6% .17 162.48);--color-emerald-600:oklch(59.6% .145 163.225);--color-emerald-700:oklch(50.8% .118 165.612);--color-emerald-800:oklch(43.2% .095 166.913);--color-emerald-900:oklch(37.8% .077 168.94);--color-blue-50:oklch(97% .014 254.604);--color-blue-100:oklch(93.2% .032 255.585);--color-blue-200:oklch(88.2% .059 254.128);--color-blue-300:oklch(80.9% .105 251.813);--color-blue-400:oklch(70.7% .165 254.624);--color-blue-500:oklch(62.3% .214 259.815);--color-blue-600:oklch(54.6% .245 262.881);--color-blue-700:oklch(48.8% .243 264.376);--color-blue-800:oklch(42.4% .199 265.638);--color-blue-900:oklch(37.9% .146 265.522);--color-purple-100:oklch(94.6% .033 307.174);--color-purple-400:oklch(71.4% .203 305.504);--color-purple-500:oklch(62.7% .265 303.9);--color-purple-600:oklch(55.8% .288 302.321);--color-purple-900:oklch(38.1% .176 304.987);--color-gray-50:oklch(98.5% .002 247.839);--color-gray-100:oklch(96.7% .003 264.542);--color-gray-200:oklch(92.8% .006 264.531);--color-gray-300:oklch(87.2% .01 258.338);--color-gray-400:oklch(70.7% .022 261.325);--color-gray-500:oklch(55.1% .027 264.364);--color-gray-600:oklch(44.6% .03 256.802);--color-gray-700:oklch(37.3% .034 259.733);--color-gray-800:oklch(27.8% .033 256.848);--color-gray-900:oklch(21% .034 264.665);--color-stone-50:oklch(98.5% .001 106.423);--color-stone-100:oklch(97% .001 106.424);--color-stone-200:oklch(92.3% .003 48.717);--color-stone-300:oklch(86.9% .005 56.366);--color-stone-400:oklch(70.9% .01 56.259);--color-stone-500:oklch(55.3% .013 58.071);--color-stone-600:oklch(44.4% .011 73.639);--color-stone-700:oklch(37.4% .01 67.558);--color-stone-800:oklch(26.8% .007 34.298);--color-stone-900:oklch(21.6% .006 56.043);--color-black:#000;--color-white:#fff;--spacing:.25rem;--container-md:28rem;--container-2xl:42rem;--container-3xl:48rem;--container-4xl:56rem;--container-5xl:64rem;--container-7xl:80rem;--text-xs:.75rem;--text-xs--line-height:calc(1 / .75);--text-sm:.875rem;--text-sm--line-height:calc(1.25 / .875);--text-base:1rem;--text-base--line-height:calc(1.5 / 1);--text-lg:1.125rem;--text-lg--line-height:calc(1.75 / 1.125);--text-xl:1.25rem;--text-xl--line-height:calc(1.75 / 1.25);--text-2xl:1.5rem;--text-2xl--line-height:calc(2 / 1.5);--text-3xl:1.875rem;--text-3xl--line-height:calc(2.25 / 1.875);--font-weight-normal:400;--font-weight-medium:500;--font-weight-semibold:600;--font-weight-bold:700;--tracking-tight:-.025em;--tracking-wider:.05em;--radius-sm:.25rem;--radius-md:.375rem;--radius-lg:.5rem;--animate-spin:spin 1s linear infinite;--animate-pulse:pulse 2s cubic-bezier(.4, 0, .6, 1) infinite;--default-transition-duration:.15s;--default-transition-timing-function:cubic-bezier(.4, 0, .2, 1);--default-font-family:var(--font-sans);--default-mono-font-family:var(--font-mono);--radius-circle:9999px}}@layer base{*,:after,:before,::backdrop{box-sizing:border-box;border:0 solid;margin:0;padding:0}::file-selector-button{box-sizing:border-box;border:0 solid;margin:0;padding:0}html,:host{-webkit-text-size-adjust:100%;tab-size:4;line-height:1.5;font-family:var(--default-font-family,ui-sans-serif, system-ui, sans-serif, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol", "Noto Color Emoji");font-feature-settings:var(--default-font-feature-settings,normal);font-variation-settings:var(--default-font-variation-settings,normal);-webkit-tap-highlight-color:transparent}hr{height:0;color:inherit;border-top-width:1px}abbr:where([title]){-webkit-text-decoration:underline dotted;text-decoration:underline dotted}h1,h2,h3,h4,h5,h6{font-size:inherit;font-weight:inherit}a{color:inherit;-webkit-text-decoration:inherit;-webkit-text-decoration:inherit;-webkit-text-decoration:inherit;text-decoration:inherit}b,strong{font-weight:bolder}code,kbd,samp,pre{font-family:var(--default-mono-font-family,ui-monospace, SFMono-Regular, Menlo, Monaco, Consolas, "Liberation Mono", "Courier New", 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transparent)}}}textarea{resize:vertical}::-webkit-search-decoration{-webkit-appearance:none}::-webkit-date-and-time-value{min-height:1lh;text-align:inherit}::-webkit-datetime-edit{display:inline-flex}::-webkit-datetime-edit-fields-wrapper{padding:0}::-webkit-datetime-edit{padding-block:0}::-webkit-datetime-edit-year-field{padding-block:0}::-webkit-datetime-edit-month-field{padding-block:0}::-webkit-datetime-edit-day-field{padding-block:0}::-webkit-datetime-edit-hour-field{padding-block:0}::-webkit-datetime-edit-minute-field{padding-block:0}::-webkit-datetime-edit-second-field{padding-block:0}::-webkit-datetime-edit-millisecond-field{padding-block:0}::-webkit-datetime-edit-meridiem-field{padding-block:0}::-webkit-calendar-picker-indicator{line-height:1}:-moz-ui-invalid{box-shadow:none}button,input:where([type=button],[type=reset],[type=submit]){appearance:button}::file-selector-button{appearance:button}::-webkit-inner-spin-button{height:auto}::-webkit-outer-spin-button{height:auto}[hidden]:where(:not([hidden=until-found])){display:none!important}button{cursor:pointer}button:disabled{cursor:not-allowed}}@layer 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var(--color-border-muted);padding-bottom:.3em;font-size:1.5em;font-weight:600}.wmde-markdown h3{font-size:1.25em;font-weight:600}.wmde-markdown h4{font-size:1em;font-weight:600}.wmde-markdown h5{font-size:.875em;font-weight:600}.wmde-markdown h6{color:var(--color-fg-muted);font-size:.85em;font-weight:600}.wmde-markdown p{margin-top:0;margin-bottom:10px}.wmde-markdown blockquote{color:var(--color-fg-muted);border-left:.25em solid var(--color-border-default);margin:0;padding:0 1em}.wmde-markdown ul,.wmde-markdown ol{margin-top:0;margin-bottom:0;padding-left:2em}.wmde-markdown ol ol,.wmde-markdown ul ol{list-style-type:lower-roman}.wmde-markdown ul ul ol,.wmde-markdown ul ol ol,.wmde-markdown ol ul ol,.wmde-markdown ol ol ol{list-style-type:lower-alpha}.wmde-markdown dd{margin-left:0}.wmde-markdown tt,.wmde-markdown code{font-family:ui-monospace,SFMono-Regular,SF Mono,Menlo,Consolas,Liberation Mono,monospace;font-size:12px}.wmde-markdown pre{word-wrap:normal;margin-top:0;margin-bottom:0;font-family:ui-monospace,SFMono-Regular,SF Mono,Menlo,Consolas,Liberation Mono,monospace;font-size:12px}.wmde-markdown .octicon{vertical-align:text-bottom;fill:currentColor;display:inline-block;overflow:visible!important}.wmde-markdown ::placeholder{color:var(--color-fg-subtle);opacity:1}.wmde-markdown input::-webkit-outer-spin-button{appearance:none;margin:0}.wmde-markdown input::-webkit-inner-spin-button{appearance:none;margin:0}.wmde-markdown [data-catalyst]{display:block}.wmde-markdown:before{content:"";display:table}.wmde-markdown:after{clear:both;content:"";display:table}.wmde-markdown>:first-child{margin-top:0!important}.wmde-markdown>:last-child{margin-bottom:0!important}.wmde-markdown a:not([href]){color:inherit;text-decoration:none}.wmde-markdown .absent{color:var(--color-danger-fg)}.wmde-markdown a.anchor{float:left;margin-left:-20px;padding-right:4px;line-height:1}.wmde-markdown .anchor:focus{outline:none}.wmde-markdown p,.wmde-markdown blockquote,.wmde-markdown ul,.wmde-markdown ol,.wmde-markdown dl,.wmde-markdown table,.wmde-markdown pre,.wmde-markdown details{margin-top:0;margin-bottom:16px}.wmde-markdown blockquote>:first-child{margin-top:0}.wmde-markdown blockquote>:last-child{margin-bottom:0}.wmde-markdown sup>a:before{content:"["}.wmde-markdown sup>a:after{content:"]"}.wmde-markdown h1 .octicon-link,.wmde-markdown h2 .octicon-link,.wmde-markdown h3 .octicon-link,.wmde-markdown h4 .octicon-link,.wmde-markdown h5 .octicon-link,.wmde-markdown h6 .octicon-link{color:var(--color-fg-default);vertical-align:middle;visibility:hidden}.wmde-markdown h1:hover .anchor,.wmde-markdown h2:hover .anchor,.wmde-markdown h3:hover .anchor,.wmde-markdown h4:hover .anchor,.wmde-markdown h5:hover .anchor,.wmde-markdown h6:hover .anchor{text-decoration:none}.wmde-markdown h1:hover .anchor .octicon-link,.wmde-markdown h2:hover .anchor .octicon-link,.wmde-markdown h3:hover .anchor .octicon-link,.wmde-markdown h4:hover .anchor .octicon-link,.wmde-markdown h5:hover .anchor .octicon-link,.wmde-markdown h6:hover .anchor .octicon-link{visibility:visible}.wmde-markdown h1 tt,.wmde-markdown h1 code,.wmde-markdown h2 tt,.wmde-markdown h2 code,.wmde-markdown h3 tt,.wmde-markdown h3 code,.wmde-markdown h4 tt,.wmde-markdown h4 code,.wmde-markdown h5 tt,.wmde-markdown h5 code,.wmde-markdown h6 tt,.wmde-markdown h6 code{font-size:inherit;padding:0 .2em}.wmde-markdown ul.no-list,.wmde-markdown ol.no-list{padding:0;list-style-type:none}.wmde-markdown ol[type="1"]{list-style-type:decimal}.wmde-markdown ol[type=a]{list-style-type:lower-alpha}.wmde-markdown ol[type=i]{list-style-type:lower-roman}.wmde-markdown div>ol:not([type]){list-style-type:decimal}.wmde-markdown ul ul,.wmde-markdown ul ol,.wmde-markdown ol ol,.wmde-markdown ol ul{margin-top:0;margin-bottom:0}.wmde-markdown li>p{margin-top:16px}.wmde-markdown li+li{margin-top:.25em}.wmde-markdown dl{padding:0}.wmde-markdown dl dt{margin-top:16px;padding:0;font-size:1em;font-style:italic;font-weight:600}.wmde-markdown dl dd{margin-bottom:16px;padding:0 16px}.wmde-markdown table th{font-weight:600}.wmde-markdown table th,.wmde-markdown table td{border:1px solid var(--color-border-default);padding:6px 13px}.wmde-markdown table tr{background-color:var(--color-canvas-default);border-top:1px solid var(--color-border-muted)}.wmde-markdown table tr:nth-child(2n){background-color:var(--color-canvas-subtle)}.wmde-markdown table img{background-color:#0000}.wmde-markdown img[align=right]{padding-left:20px}.wmde-markdown img[align=left]{padding-right:20px}.wmde-markdown .emoji{vertical-align:text-top;background-color:#0000;max-width:none}.wmde-markdown span.frame{display:block;overflow:hidden}.wmde-markdown span.frame>span{float:left;border:1px solid var(--color-border-default);width:auto;margin:13px 0 0;padding:7px;display:block;overflow:hidden}.wmde-markdown span.frame span img{float:left;display:block}.wmde-markdown 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tt{background-color:var(--color-neutral-muted);border-radius:6px;margin:0;padding:.2em .4em;font-size:85%}.wmde-markdown code br,.wmde-markdown tt br{display:none}.wmde-markdown del code{-webkit-text-decoration:inherit;-webkit-text-decoration:inherit;text-decoration:inherit}.wmde-markdown pre code{font-size:100%}.wmde-markdown pre>code{word-break:normal;white-space:pre;background:0 0;border:0;margin:0;padding:0}.wmde-markdown pre{background-color:var(--color-canvas-subtle);border-radius:6px;font-size:85%;line-height:1.45}.wmde-markdown pre code,.wmde-markdown pre tt{max-width:auto;line-height:inherit;word-wrap:normal;background-color:#0000;border:0;margin:0;padding:0;display:inline;overflow:visible}.wmde-markdown pre>code{padding:16px;display:block;overflow:auto}.wmde-markdown pre>code::-webkit-scrollbar{background:0 0;width:8px;height:8px}.wmde-markdown pre>code::-webkit-scrollbar-thumb{background:var(--color-fg-muted);border-radius:10px}.wmde-markdown .csv-data td,.wmde-markdown .csv-data th{text-align:left;white-space:nowrap;padding:5px;font-size:12px;line-height:1;overflow:hidden}.wmde-markdown .csv-data .blob-num{text-align:right;background:var(--color-canvas-default);border:0;padding:10px 8px 9px}.wmde-markdown .csv-data tr{border-top:0}.wmde-markdown .csv-data th{background:var(--color-canvas-subtle);border-top:0;font-weight:600}.wmde-markdown .footnotes{color:var(--color-fg-muted);border-top:1px solid var(--color-border-default);font-size:12px}.wmde-markdown .footnotes ol{padding-left:16px}.wmde-markdown .footnotes li{position:relative}.wmde-markdown .footnotes li:target:before{pointer-events:none;content:"";border:2px solid var(--color-accent-emphasis);border-radius:6px;position:absolute;inset:-8px -8px -8px -24px}.wmde-markdown .footnotes li:target{color:var(--color-fg-default)}.wmde-markdown .footnotes .data-footnote-backref g-emoji{font-family:monospace}.wmde-markdown .task-list-item{list-style-type:none}.wmde-markdown .task-list-item 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.markdown-alert-title{color:var(--fgColor-attention,var(--color-attention-fg))}.wmde-markdown .markdown-alert.markdown-alert-caution{border-left-color:var(--borderColor-danger-emphasis,var(--color-danger-emphasis))}.wmde-markdown .markdown-alert.markdown-alert-caution .markdown-alert-title{color:var(--fgColor-danger,var(--color-danger-fg))}.wmde-markdown .highlight-line{background-color:var(--color-neutral-muted)}.wmde-markdown .code-line.line-number:before{text-align:right;width:1rem;color:var(--color-fg-subtle);content:attr(line);white-space:nowrap;margin-right:16px;display:inline-block}.wmde-markdown .token.comment,.wmde-markdown .token.prolog,.wmde-markdown .token.doctype,.wmde-markdown .token.cdata{color:var(--color-prettylights-syntax-comment)}.wmde-markdown .token.namespace{opacity:.7}.wmde-markdown .token.property,.wmde-markdown .token.tag,.wmde-markdown .token.selector,.wmde-markdown .token.constant,.wmde-markdown .token.symbol,.wmde-markdown 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--tw-gradient-to{syntax:"<color>";inherits:false;initial-value:#0000}@property --tw-gradient-stops{syntax:"*";inherits:false}@property --tw-gradient-via-stops{syntax:"*";inherits:false}@property --tw-gradient-from-position{syntax:"<length-percentage>";inherits:false;initial-value:0%}@property --tw-gradient-via-position{syntax:"<length-percentage>";inherits:false;initial-value:50%}@property --tw-gradient-to-position{syntax:"<length-percentage>";inherits:false;initial-value:100%}@property --tw-leading{syntax:"*";inherits:false}@property --tw-font-weight{syntax:"*";inherits:false}@property --tw-tracking{syntax:"*";inherits:false}@property --tw-ordinal{syntax:"*";inherits:false}@property --tw-slashed-zero{syntax:"*";inherits:false}@property --tw-numeric-figure{syntax:"*";inherits:false}@property --tw-numeric-spacing{syntax:"*";inherits:false}@property --tw-numeric-fraction{syntax:"*";inherits:false}@property --tw-shadow{syntax:"*";inherits:false;initial-value:0 0 #0000}@property 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\ No newline at end of file
diff --git a/src/web/utils/paste-as-markdown.ts b/src/web/utils/paste-as-markdown.ts
new file mode 100644
index 000000000..9185b648f
--- /dev/null
+++ b/src/web/utils/paste-as-markdown.ts
@@ -0,0 +1,452 @@
+import TurndownService from "turndown";
+import { gfm } from "turndown-plugin-gfm";
+
+const turndownService = new TurndownService({
+	headingStyle: "atx",
+	bulletListMarker: "-",
+	codeBlockStyle: "fenced",
+	strongDelimiter: "**",
+	emDelimiter: "*",
+	fence: "```",
+});
+
+// Enable GFM extensions (tables, strikethrough, task lists)
+turndownService.use(gfm);
+
+// Remove Word-specific noise tags
+turndownService.remove(["style", "meta", "link", "script"]);
+
+// Keep <br> as raw HTML so it works inside Markdown table cells.
+// Turndown's default turns <br> into "  \n" which breaks table rows.
+turndownService.addRule("keepBr", {
+	filter: "br",
+	replacement: () => "<br>",
+});
+
+/**
+ * Clean and normalise HTML (especially from Word / docx sources) so that
+ * Turndown produces clean Markdown.
+ *
+ * Handles:
+ * - Word mso-list paragraphs → <ul><li>
+ * - Inline style → semantic tag conversion (bold, italic, underline)
+ * - Table cell flattening (unwraps <p>, <div> inside <td>/<th>)
+ * - First table row promoted to <th> for GFM table support
+ * - Removal of noise tags, classes, and empty elements
+ */
+export async function cleanHtml(html: string, options?: { keepMedia?: boolean }): Promise<string> {
+	const parser = new DOMParser();
+	const doc = parser.parseFromString(html, "text/html");
+
+	// Remove noise tags
+	for (const tag of ["style", "meta", "link", "script", "colgroup", "col"]) {
+		for (const el of Array.from(doc.querySelectorAll(tag))) {
+			el.remove();
+		}
+	}
+
+	// Word encodes bullet lists as <p style="mso-list:..."> with a conditional
+	// comment wrapper. Process these before wiping inline styles.
+	const msoListParas = Array.from(
+		doc.querySelectorAll('p[style*="mso-list"], div[style*="mso-list"]'),
+	) as HTMLElement[];
+	if (msoListParas.length > 0) {
+		const clusters: HTMLElement[][] = [];
+		let current: HTMLElement[] = [];
+		for (const el of msoListParas) {
+			if (current.length === 0) {
+				current.push(el);
+			} else {
+				const last = current[current.length - 1]!;
+				let next = last.nextSibling;
+				let adjacent = false;
+				while (next) {
+					if (next.nodeType === Node.ELEMENT_NODE) {
+						adjacent = next === el;
+						break;
+					}
+					if (next.nodeType === Node.TEXT_NODE && next.textContent?.trim()) {
+						break;
+					}
+					next = next.nextSibling;
+				}
+				if (adjacent) {
+					current.push(el);
+				} else {
+					clusters.push(current);
+					current = [el];
+				}
+			}
+		}
+		if (current.length > 0) clusters.push(current);
+
+		for (const cluster of clusters) {
+			const ul = doc.createElement("ul");
+			const first = cluster[0]!;
+			for (const el of cluster) {
+				for (const ignore of Array.from(el.querySelectorAll('[style*="mso-list:Ignore"]'))) {
+					ignore.remove();
+				}
+				for (const child of Array.from(el.querySelectorAll("o\\:p, o\\:P"))) {
+					child.remove();
+				}
+				const li = doc.createElement("li");
+				while (el.firstChild) {
+					li.appendChild(el.firstChild);
+				}
+				ul.appendChild(li);
+				if (el !== first) {
+					el.remove();
+				}
+			}
+			if (first.parentNode) {
+				first.parentNode.insertBefore(ul, first);
+				first.remove();
+			}
+		}
+	}
+
+	// Remove mso- classes and all other classes (Markdown doesn't need them)
+	for (const el of Array.from(doc.querySelectorAll("[class]"))) {
+		el.removeAttribute("class");
+	}
+
+	// Convert inline styles that carry semantic meaning to actual tags
+	for (const el of Array.from(doc.querySelectorAll("[style]"))) {
+		const raw = el.getAttribute("style") || "";
+		const rules = new Map<string, string>();
+		for (const part of raw.split(";")) {
+			const idx = part.indexOf(":");
+			if (idx > 0) {
+				rules.set(
+					part.slice(0, idx).trim().toLowerCase(),
+					part
+						.slice(idx + 1)
+						.trim()
+						.toLowerCase(),
+				);
+			}
+		}
+
+		const alreadyWrapped = (tag: string): boolean => {
+			return el.tagName === tag || el.closest(tag) !== null || el.querySelector(tag) !== null;
+		};
+
+		const fw = rules.get("font-weight");
+		if (
+			(fw === "bold" || fw === "700" || fw === "800" || fw === "900") &&
+			!alreadyWrapped("strong") &&
+			!alreadyWrapped("b")
+		) {
+			const wrap = doc.createElement("strong");
+			while (el.firstChild) wrap.appendChild(el.firstChild);
+			el.appendChild(wrap);
+		}
+
+		const fs = rules.get("font-style");
+		if (fs === "italic" && !alreadyWrapped("em") && !alreadyWrapped("i")) {
+			const wrap = doc.createElement("em");
+			while (el.firstChild) wrap.appendChild(el.firstChild);
+			el.appendChild(wrap);
+		}
+
+		const td = rules.get("text-decoration");
+		if (td?.includes("underline") && !alreadyWrapped("u")) {
+			const wrap = doc.createElement("u");
+			while (el.firstChild) wrap.appendChild(el.firstChild);
+			el.appendChild(wrap);
+		}
+		if (td?.includes("line-through") && !alreadyWrapped("s") && !alreadyWrapped("del") && !alreadyWrapped("strike")) {
+			const wrap = doc.createElement("s");
+			while (el.firstChild) wrap.appendChild(el.firstChild);
+			el.appendChild(wrap);
+		}
+
+		el.removeAttribute("style");
+	}
+
+	// Drop Word-specific XML tags like <o:p>
+	for (const el of Array.from(doc.querySelectorAll("o\\:p, o\\:P"))) {
+		el.remove();
+	}
+
+	// Remove empty block/inline elements that Word loves to generate.
+	// In docx-upload mode (keepMedia=true) we preserve elements that contain
+	// media so server-side extracted images aren't stripped.
+	for (const selector of ["p", "span", "font", "div"]) {
+		for (const el of Array.from(doc.querySelectorAll(selector))) {
+			const hasMedia = !!el.querySelector("img, video, audio, iframe, canvas, svg");
+			if (!el.textContent?.trim() && !(options?.keepMedia && hasMedia)) {
+				el.remove();
+			}
+		}
+	}
+
+	// Plain paragraphs that start with a Unicode bullet char (not mso-list)
+	// also need conversion so Turndown produces "- item" syntax.
+	const BULLET_RE =
+		/^[\s\u2022\u25cf\u00b7\u25cb\u25e6\u2219\u2023\uf06c\uf0b7\uf0a7\u25aa\u25ab\u2013\u2014\u2794\u27a2]+/;
+	const bulletCandidates = Array.from(doc.querySelectorAll("p, div")).filter(
+		(el) => !el.closest("ul, ol, table") && BULLET_RE.test(el.textContent || ""),
+	) as HTMLElement[];
+
+	if (bulletCandidates.length > 0) {
+		const clusters: HTMLElement[][] = [];
+		let current: HTMLElement[] = [];
+		for (const el of bulletCandidates) {
+			if (current.length === 0) {
+				current.push(el);
+			} else {
+				const last = current[current.length - 1]!;
+				let next = last.nextSibling;
+				let adjacent = false;
+				while (next) {
+					if (next.nodeType === Node.ELEMENT_NODE) {
+						adjacent = next === el;
+						break;
+					}
+					if (next.nodeType === Node.TEXT_NODE && next.textContent?.trim()) {
+						break;
+					}
+					next = next.nextSibling;
+				}
+				if (adjacent) {
+					current.push(el);
+				} else {
+					clusters.push(current);
+					current = [el];
+				}
+			}
+		}
+		if (current.length > 0) clusters.push(current);
+
+		for (const cluster of clusters) {
+			const ul = doc.createElement("ul");
+			for (const el of cluster) {
+				const li = doc.createElement("li");
+				let text = el.textContent || "";
+				text = text.replace(BULLET_RE, "").trim();
+				if (text) {
+					li.textContent = text;
+				}
+				ul.appendChild(li);
+				el.remove();
+			}
+			const first = cluster[0]!;
+			if (first.parentNode) {
+				first.parentNode.insertBefore(ul, first);
+			}
+		}
+	}
+
+	// Normalise tables for Markdown conversion:
+	// 1. Recursively unwrap any block-level elements inside cells.
+	//    Word loves wrapping cell content in <p>, <div>, <section>, etc.
+	//    Turndown treats those as block paragraphs (\n\n) which breaks
+	//    Markdown table syntax — every cell must stay on a single line.
+	// 2. Collapse whitespace inside every cell.
+	// 3. Ensure the first row uses <th> so turndown-plugin-gfm recognises
+	//    the table heading.
+	const inlineTags = new Set([
+		"A",
+		"ABBR",
+		"B",
+		"BDI",
+		"BDO",
+		"BR",
+		"CITE",
+		"CODE",
+		"DATA",
+		"DEL",
+		"DFN",
+		"EM",
+		"I",
+		"INS",
+		"KBD",
+		"MARK",
+		"Q",
+		"RUBY",
+		"S",
+		"SAMP",
+		"SMALL",
+		"SPAN",
+		"STRIKE",
+		"STRONG",
+		"SUB",
+		"SUP",
+		"TIME",
+		"U",
+		"VAR",
+		"WBR",
+	]);
+
+	for (const table of Array.from(doc.querySelectorAll("table"))) {
+		for (const cell of Array.from(table.querySelectorAll("td, th"))) {
+			// Flatten lists inside table cells into prefixed paragraphs.
+			for (const list of Array.from(cell.querySelectorAll("ul, ol"))) {
+				const isOrdered = list.tagName === "OL";
+				let index = 1;
+				const fragment = doc.createDocumentFragment();
+				for (const item of Array.from(list.querySelectorAll("li"))) {
+					for (const p of Array.from(item.querySelectorAll("p"))) {
+						const pFrag = doc.createDocumentFragment();
+						while (p.firstChild) pFrag.appendChild(p.firstChild);
+						p.replaceWith(pFrag);
+					}
+					const p = doc.createElement("p");
+					const prefix = isOrdered ? `${index}. ` : "";
+					p.innerHTML = prefix + item.innerHTML.trim();
+					fragment.appendChild(p);
+					index++;
+				}
+				list.replaceWith(fragment);
+			}
+
+			// Recursively unwrap non-inline elements until only inline
+			// tags and text nodes remain.
+			let changed = true;
+			while (changed) {
+				changed = false;
+				for (const el of Array.from(cell.querySelectorAll("*"))) {
+					if (!inlineTags.has(el.tagName)) {
+						const fragment = doc.createDocumentFragment();
+						while (el.firstChild) {
+							fragment.appendChild(el.firstChild);
+						}
+						if (el.tagName === "P") {
+							fragment.appendChild(doc.createElement("br"));
+						}
+						el.replaceWith(fragment);
+						changed = true;
+						break;
+					}
+				}
+			}
+			let html = cell.innerHTML;
+			html = html.trim().replace(/\s+/g, " ");
+			html = html.replace(/(\s*<br>)+\s*$/i, "");
+			cell.innerHTML = html;
+		}
+
+		const firstRow = table.querySelector("tr");
+		if (firstRow) {
+			for (const td of Array.from(firstRow.querySelectorAll("td"))) {
+				const th = doc.createElement("th");
+				th.innerHTML = td.innerHTML;
+				for (const attr of Array.from(td.attributes)) {
+					th.setAttribute(attr.name, attr.value);
+				}
+				td.replaceWith(th);
+			}
+		}
+	}
+
+	return doc.body.innerHTML.trim();
+}
+
+/**
+ * Convert rich-text HTML on the clipboard to Markdown.
+ *
+ * @returns the Markdown string when conversion succeeded and differs from
+ *          plain text; `null` when there is no rich-text benefit.
+ */
+export type ImageUploader = (source: Blob | string) => Promise<string | null>;
+
+export async function handlePasteAsMarkdown(
+	e: React.ClipboardEvent<HTMLTextAreaElement>,
+	uploadImage?: ImageUploader,
+): Promise<string | null> {
+	const html = e.clipboardData.getData("text/html");
+	const plainText = e.clipboardData.getData("text/plain");
+
+	// No HTML on the clipboard → no rich-text benefit.
+	if (!html || html.trim().length === 0) {
+		return null;
+	}
+
+	const cleanedHtml = await cleanHtml(html);
+	if (!cleanedHtml || cleanedHtml.trim().length === 0) {
+		return null;
+	}
+
+	let processedHtml = cleanedHtml;
+
+	// Process images in the HTML before converting to Markdown.
+	if (uploadImage) {
+		const parser = new DOMParser();
+		const doc = parser.parseFromString(cleanedHtml, "text/html");
+		const images = Array.from(doc.querySelectorAll("img"));
+		if (images.length > 0) {
+			await Promise.all(
+				images.map(async (img) => {
+					const src = img.getAttribute("src") || "";
+					if (!src) {
+						img.remove();
+						return;
+					}
+					// Reject file:// and relative paths that aren't data URIs or HTTP(S)
+					if (!src.startsWith("data:") && !src.startsWith("http://") && !src.startsWith("https://")) {
+						img.remove();
+						return;
+					}
+					try {
+						const newUrl = await uploadImage(src);
+						if (newUrl) {
+							img.setAttribute("src", newUrl);
+						} else {
+							img.remove();
+						}
+					} catch {
+						img.remove();
+					}
+				}),
+			);
+			processedHtml = doc.body.innerHTML.trim();
+		}
+	}
+
+	let markdown: string;
+	try {
+		markdown = turndownService.turndown(processedHtml);
+	} catch {
+		return null;
+	}
+
+	// Move whitespace that sits *inside* bold/italic markers to the
+	// outside so the markers hug the actual text.
+	// "**  text **"  → " **text** "
+	// "**text **"    → "**text** "
+	// "** text**"    → " **text**"
+	let prev: string;
+	do {
+		prev = markdown;
+		markdown = markdown.replace(/\*\*(\s*)([^\n]*?)(\s*)\*\*/g, "$1**$2**$3");
+	} while (markdown !== prev);
+
+	// Same for italic (single asterisk) — be careful not to touch list bullets.
+	// We only match when both opening and closing * are present around content.
+	do {
+		prev = markdown;
+		markdown = markdown.replace(/(?<!\*)\*(\s*)([^\s*][^\n]*?[^\s*])(\s*)\*(?!\*)/g, "$1*$2*$3");
+	} while (markdown !== prev);
+
+	// Ensure a space after bold/italic closers when they touch plain text.
+	// "**text**word" → "**text** word"
+	// "*text*word"   → "*text* word"
+	markdown = markdown.replace(/\*\*([^\s][^\n]*?)\*\*([^\s*<|\n\r])/g, "**$1** $2");
+	markdown = markdown.replace(/(?<!\*)\*([^\s*][^\n]*?)\*([^\s*<|\n\r])(?!\*)/g, "*$1* $2");
+
+	// Ensure ordered-list markers are followed by a space so parsers recognise
+	// them correctly (e.g. Word sometimes produces "1.•item").
+	markdown = markdown.replace(/(^|\s)(\d+\.)([^\s\d])/g, "$1$2 $3");
+
+	// If the converted Markdown is structurally identical to the plain-text
+	// version there is no rich-text benefit; fall back to the native paste.
+	const normalizedMd = markdown.trim().replace(/\s+/g, " ");
+	const normalizedPlain = plainText.trim().replace(/\s+/g, " ");
+	if (normalizedMd === normalizedPlain) {
+		return null;
+	}
+
+	return markdown;
+}