diff --git a/apps/desktop/src/components/assistant-ui/markdown-text.filelinks.test.tsx b/apps/desktop/src/components/assistant-ui/markdown-text.filelinks.test.tsx
new file mode 100644
index 0000000000..ed0e9ebf04
--- /dev/null
+++ b/apps/desktop/src/components/assistant-ui/markdown-text.filelinks.test.tsx
@@ -0,0 +1,62 @@
+import { cleanup, render, screen, waitFor } from '@testing-library/react'
+import { afterEach, describe, expect, it } from 'vitest'
+
+import { MarkdownTextContent } from './markdown-text'
+
+// Regression for #82140: a plain filesystem href in assistant markdown
+// (`[report](/home/user/report.md)`) rendered as a bare dead anchor —
+// file:// is blocked in the renderer, and on a remote gateway the path
+// isn't on this disk at all. Such links must route through the preview
+// pipeline (PreviewAttachment → normalizeOrLocalPreviewTarget), which
+// resolves the path at VIEW time against the session's backend: local
+// connections read the file directly, remote connections fetch it over the
+// authenticated /api/fs bridge. Media-extension paths keep their inline
+// player instead.
+describe('MarkdownLink filesystem hrefs', () => {
+  afterEach(cleanup)
+
+  it('routes an absolute file path link through the preview attachment', async () => {
+    render(<MarkdownTextContent isRunning={false} text="Wrote it: [report](/home/user/report.md)" />)
+
+    // PreviewAttachment paints the filename + an Open preview button —
+    // that's the view-time door, not a dead <a>.
+    await screen.findByText('report.md')
+    expect(screen.getByRole('button', { name: 'Open preview' })).toBeTruthy()
+    expect(document.querySelector('a[href="/home/user/report.md"]')).toBeNull()
+  })
+
+  it('routes file:// and ~/ links the same way', async () => {
+    render(
+      <MarkdownTextContent
+        isRunning={false}
+        text={'See [notes](file:///srv/data/notes.txt) and [todo](~/todo.md)'}
+      />
+    )
+
+    await screen.findByText('notes.txt')
+    await screen.findByText('todo.md')
+    expect(screen.getAllByRole('button', { name: 'Open preview' })).toHaveLength(2)
+  })
+
+  it('renders a media player for a media-extension path link', async () => {
+    const { container } = render(<MarkdownTextContent isRunning={false} text="[clip](/tmp/demo.mp4)" />)
+
+    await waitFor(() => expect(container.querySelector('video')).not.toBeNull())
+    expect(container.querySelector('a[href="/tmp/demo.mp4"]')).toBeNull()
+  })
+
+  it('leaves anchors and relative links out of the preview pipeline', () => {
+    render(
+      <MarkdownTextContent
+        isRunning={false}
+        text={'[frag](#section-2) and [rel](docs/guide.md) and [site](https://example.com)'}
+      />
+    )
+
+    // Fragment anchors survive untouched; relative links are NOT rewritten
+    // (they keep Streamdown's pre-existing handling) — neither gains a
+    // preview affordance.
+    expect(screen.queryByRole('button', { name: 'Open preview' })).toBeNull()
+    expect(document.querySelector('a[href="#section-2"]')).not.toBeNull()
+  })
+})
diff --git a/apps/desktop/src/components/assistant-ui/markdown-text.tsx b/apps/desktop/src/components/assistant-ui/markdown-text.tsx
index f9eb78084a..54e7f04569 100644
--- a/apps/desktop/src/components/assistant-ui/markdown-text.tsx
+++ b/apps/desktop/src/components/assistant-ui/markdown-text.tsx
@@ -22,6 +22,7 @@ import { parseMarkdownIntoBlocksCached } from '@/lib/markdown-blocks'
 import { preprocessMarkdown } from '@/lib/markdown-preprocess'
 import {
   downloadGatewayMediaFile,
+  isFileMediaPath,
   isInlineMediaSrc,
   isMarkdownDocumentPath,
   isRemoteGateway,
@@ -282,6 +283,25 @@ function MarkdownLink({ children, className, href, ...props }: ComponentProps<'a
   const target = href ? normalizeExternalUrl(href) : href
 
   if (!target || !/^https?:\/\//i.test(target)) {
+    // A plain filesystem href (`[report](/home/user/report.md)`, `file://…`,
+    // `~/notes.md`, `C:\…`) names a file on the AGENT's machine. A bare
+    // anchor is a dead link there — file:// is blocked in the renderer, and
+    // on a remote gateway the path isn't even on this disk. Route it through
+    // the preview pipeline instead: normalizeOrLocalPreviewTarget resolves at
+    // VIEW time against the session's backend (local reads the file directly;
+    // remote fetches it over the authenticated /api/fs bridge), so the same
+    // transcript works from every machine that opens it. Media extensions
+    // keep their richer inline player.
+    const fileHref = href && !href.startsWith('#') && isFileMediaPath(href) ? href : null
+
+    if (fileHref) {
+      return mediaKind(fileHref) === 'file' ? (
+        <PreviewAttachment source="explicit-link" target={fileHref} />
+      ) : (
+        <MediaAttachment path={fileHref} />
+      )
+    }
+
     return (
       <a
         className={cn('ref wrap-anywhere', className)}
diff --git a/apps/desktop/src/lib/markdown-preprocess.ts b/apps/desktop/src/lib/markdown-preprocess.ts
index cbecf243c5..5959048120 100644
--- a/apps/desktop/src/lib/markdown-preprocess.ts
+++ b/apps/desktop/src/lib/markdown-preprocess.ts
@@ -2,6 +2,8 @@ import { normalizeMathDelimiters } from '@assistant-ui/react-streamdown'
 
 import { isLikelyProseFence, sanitizeLanguageTag } from '@/lib/markdown-code'
 import { clampHtmlNestingDepth } from '@/lib/markdown-html-depth'
+import { mediaKind, mediaMarkdownHref } from '@/lib/media'
+import { previewMarkdownHref } from '@/lib/preview-targets'
 import { stripPreviewTargets } from '@/lib/preview-targets'
 import { linkifySessionRefs } from '@/lib/session-refs'
 
@@ -27,6 +29,12 @@ const LOCAL_PREVIEW_URL_RE = /(^|\s)https?:\/\/(?:localhost|127\.0\.0\.1|0\.0\.0
 const LOCAL_PREVIEW_ONLY_RE = /^https?:\/\/(?:localhost|127\.0\.0\.1|0\.0\.0\.0|\[::1\])(?::\d+)?\/?$/i
 const URL_ONLY_LINE_RE = /^\s*https?:\/\/\S+\s*$/i
 const CITATION_MARKER_RE = /(?<=[\p{L}\p{N})\].,!?:;"'”’])\[(?:\d+(?:\s*,\s*\d+)*)\](?!\()/gu
+// Markdown links whose target is a filesystem path on the agent's machine:
+// `[report](/home/user/report.md)`, `[notes](file:///srv/notes.txt)`,
+// `[todo](~/todo.md)`, `[log](C:\logs\run.txt)`. Negative lookbehind keeps
+// image syntax (`![alt](path)`) on its existing inline pipeline. The target
+// char class excludes `)`/whitespace, matching how LLMs actually emit these.
+const FILE_LINK_RE = /(?<!!)\[(?<label>[^\]\n]+)\]\((?<target><?(?:file:\/\/|\/|~\/|[a-z]:[\\/])[^)\s]*>?)\)/gi
 
 /**
  * Returns true when `body` contains a line that's exactly `marker` (modulo
@@ -145,6 +153,26 @@ function autoLinkRawUrls(text: string): string {
   })
 }
 
+// Rewrite filesystem-path links to the renderer's hash-href door (#82140).
+// A plain path/file: href names a file on the AGENT's machine: Streamdown's
+// URL hardening blocks `file:`/`~/` outright, and an absolute path renders
+// as a dead anchor (file:// is blocked in the renderer; on a remote gateway
+// the file isn't on this disk at all). `#preview/…` / `#media:…` hrefs pass
+// hardening by design and route through PreviewAttachment/MediaAttachment,
+// which resolve the path at VIEW time against the session's backend — local
+// reads the file directly, remote fetches it over the authenticated /api/fs
+// bridge — so the same transcript works from every machine that opens it.
+function routeFileLinksToPreview(text: string): string {
+  return text.replace(FILE_LINK_RE, (match: string, ...args: unknown[]) => {
+    const groups = args.at(-1) as { label: string; target: string }
+    const target = groups.target.replace(/^<|>$/g, '')
+
+    const href = mediaKind(target) === 'file' ? previewMarkdownHref(target) : mediaMarkdownHref(target)
+
+    return `[${groups.label}](${href})`
+  })
+}
+
 function normalizeVisibleProse(text: string): string {
   return text
     .split(INLINE_CODE_SPLIT_RE)
@@ -153,7 +181,9 @@ function normalizeVisibleProse(text: string): string {
         ? part
         : linkifySessionRefs(
             autoLinkRawUrls(
-              part.replace(/`{3,}/g, '').replace(LOCAL_PREVIEW_URL_RE, '$1').replace(CITATION_MARKER_RE, '')
+              routeFileLinksToPreview(
+                part.replace(/`{3,}/g, '').replace(LOCAL_PREVIEW_URL_RE, '$1').replace(CITATION_MARKER_RE, '')
+              )
             )
           )
     )
diff --git a/apps/desktop/src/lib/media.ts b/apps/desktop/src/lib/media.ts
index 3bc9808aa5..a7952a0e11 100644
--- a/apps/desktop/src/lib/media.ts
+++ b/apps/desktop/src/lib/media.ts
@@ -73,7 +73,7 @@ export function isInlineMediaSrc(path: string): boolean {
   return /^(?:https?|data):/i.test(path)
 }
 
-function isFileMediaPath(path: string): boolean {
+export function isFileMediaPath(path: string): boolean {
   return /^(?:file:|\/|~\/|[a-z]:[\\/]|\\\\)/i.test(path)
 }