diff --git a/desktop/src/components/chat/AssistantMessage.tsx b/desktop/src/components/chat/AssistantMessage.tsx
index aa958abd..a6b5ac5c 100644
--- a/desktop/src/components/chat/AssistantMessage.tsx
+++ b/desktop/src/components/chat/AssistantMessage.tsx
@@ -19,11 +19,14 @@ type Props = {
   branchAction?: MessageBranchAction
   sessionId?: string
   timestamp?: number
+  /** This turn's real changed files (absolute), used to anchor output chips onto
+   *  files that were actually written instead of guessing from the prose. */
+  turnChangedFiles?: string[]
 }
 
 const MAX_CARDS = 3
 
-export const AssistantMessage = memo(function AssistantMessage({ content, isStreaming, branchAction, sessionId, timestamp }: Props) {
+export const AssistantMessage = memo(function AssistantMessage({ content, isStreaming, branchAction, sessionId, timestamp, turnChangedFiles }: Props) {
   const t = useTranslation()
   const workDir = useWorkspacePanelStore((s) => (sessionId ? s.statusBySession[sessionId]?.workDir : undefined))
 
@@ -53,10 +56,10 @@ export const AssistantMessage = memo(function AssistantMessage({ content, isStre
       isStreaming || !sessionId
         ? []
         : // Image/video targets render inline (InlineImageGallery/InlineVideoGallery); never also as a card.
-          extractAssistantOutputTargets(content, { workDir }).filter(
+          extractAssistantOutputTargets(content, { workDir, changedFiles: turnChangedFiles }).filter(
             (target) => target.kind !== 'image' && target.kind !== 'video',
           ),
-    [content, isStreaming, sessionId, workDir],
+    [content, isStreaming, sessionId, workDir, turnChangedFiles],
   )
 
   if (!content.trim()) return null
diff --git a/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx b/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
index f0733abe..2969d82d 100644
--- a/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
+++ b/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
@@ -84,6 +84,7 @@ vi.mock('../../i18n', () => ({
 // Import after mocks
 // ──────────────────────────────────────────────────────────────────────────────
 import { CurrentTurnChangeCard } from './CurrentTurnChangeCard'
+import { localFileUrl } from '../../lib/handlePreviewLink'
 import type { SessionTurnCheckpoint } from '../../api/sessions'
 
 // ──────────────────────────────────────────────────────────────────────────────
@@ -201,6 +202,24 @@ describe('CurrentTurnChangeCard – row opens the workspace diff', () => {
     expect(openPreviewSpy).toHaveBeenCalledWith('s1', 'README.md', 'diff')
   })
 
+  it('clicking an outside-workspace html changed file opens the in-app browser via local-file', () => {
+    // The file lives outside the workdir (absolute displayPath) — no diff baseline,
+    // so html renders directly in the in-app browser via the /local-file route.
+    renderCard(['/other/place/todo.html'])
+    const row = screen.getByRole('button', { name: /turnChangesOpenInWorkspaceAria/ })
+    fireEvent.click(row)
+    expect(browserOpenSpy).toHaveBeenCalledWith('s1', localFileUrl('http://127.0.0.1:4321', '/other/place/todo.html'))
+    expect(openPreviewSpy).not.toHaveBeenCalled()
+  })
+
+  it('clicking an outside-workspace non-html changed file opens a file preview (not a diff)', () => {
+    renderCard(['/other/place/notes.txt'])
+    const row = screen.getByRole('button', { name: /turnChangesOpenInWorkspaceAria/ })
+    fireEvent.click(row)
+    expect(openPreviewSpy).toHaveBeenCalledWith('s1', '/other/place/notes.txt', 'file')
+    expect(browserOpenSpy).not.toHaveBeenCalled()
+  })
+
   it('does NOT render an inline diff surface after clicking a row', () => {
     renderCard(['/w/proj/src/main.ts'])
     const row = screen.getByRole('button', { name: /turnChangesOpenInWorkspaceAria/ })
@@ -280,7 +299,9 @@ describe('CurrentTurnChangeCard – open-with buttons', () => {
     expect(openPreviewSpy).toHaveBeenCalledWith('s1', 'README.md', 'file')
   })
 
-  it('clicking project index.html open-with opens menu with workspace preview item', async () => {
+  it('clicking a standalone index.html (no manifest in change-set) offers both workspace preview and in-app browser', async () => {
+    // A hand-authored single-page index.html is statically previewable, so the
+    // menu offers the in-app browser alongside the workspace source view.
     renderCard(['/w/proj/index.html'])
     const [openWithBtn] = screen.getAllByRole('button', { name: 'openWith.title' })
 
@@ -288,6 +309,21 @@ describe('CurrentTurnChangeCard – open-with buttons', () => {
       fireEvent.click(openWithBtn!)
     })
 
+    expect(await screen.findByText('openWith.workspacePreview')).toBeInTheDocument()
+    expect(screen.queryByText('openWith.inAppBrowser')).toBeInTheDocument()
+  })
+
+  it('clicking a framework-template index.html (manifest in same change-set) hides the in-app browser', async () => {
+    // With a package.json in the same turn, the root index.html is a build
+    // template that needs a dev server — static preview would render blank — so
+    // only the workspace source view is offered.
+    renderCard(['/w/proj/index.html', '/w/proj/package.json', '/w/proj/vite.config.ts'])
+    const [openWithBtn] = screen.getAllByRole('button', { name: 'openWith.title' })
+
+    await act(async () => {
+      fireEvent.click(openWithBtn!)
+    })
+
     expect(await screen.findByText('openWith.workspacePreview')).toBeInTheDocument()
     expect(screen.queryByText('openWith.inAppBrowser')).not.toBeInTheDocument()
   })
diff --git a/desktop/src/components/chat/CurrentTurnChangeCard.tsx b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
index 28dc3a0b..896d3c7e 100644
--- a/desktop/src/components/chat/CurrentTurnChangeCard.tsx
+++ b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
@@ -6,6 +6,8 @@ import { useTranslation, type TranslationKey } from '../../i18n'
 import { OpenWithMenu } from '../common/OpenWithMenu'
 import { buildOpenWithItems, describeFileType, isPreviewableChangedFile, type OpenWithItem } from '../../lib/openWithItems'
 import { openWithContextForWorkspaceFile } from '../../lib/openWithContextForHref'
+import { isAbsoluteLocalPath, localFileUrl } from '../../lib/handlePreviewLink'
+import { shouldOfferStaticHtmlPreview } from '../../lib/htmlPreviewPolicy'
 import { getServerBaseUrl } from '../../lib/desktopRuntime'
 import { getDesktopHost } from '../../lib/desktopHost'
 import { useOpenTargetStore } from '../../stores/openTargetStore'
@@ -57,12 +59,24 @@ export function CurrentTurnChangeCard({
     ? files.slice(0, COLLAPSED_COUNT)
     : files
 
-  const openDiffInWorkspace = useCallback((fileEntry: ChangedFileEntry) => {
+  const openChangedFile = useCallback((fileEntry: ChangedFileEntry) => {
+    // A changed file outside the workdir (absolute displayPath — e.g. another
+    // drive) has no checkpoint baseline, so a diff is meaningless. Render html in
+    // the in-app browser and everything else as a file preview (served by its
+    // absolute path). In-workdir files keep the diff view.
+    if (isAbsoluteLocalPath(fileEntry.displayPath)) {
+      if (shouldOfferStaticHtmlPreview(fileEntry.displayPath, { siblingFiles: files.map((entry) => entry.displayPath) })) {
+        useBrowserPanelStore.getState().open(sessionId, localFileUrl(getServerBaseUrl(), fileEntry.apiPath))
+        return
+      }
+      void useWorkspacePanelStore.getState().openPreview(sessionId, fileEntry.displayPath, 'file')
+      return
+    }
     // Jump to the right-side workspace and open a diff tab. We pass the workDir-relative
     // path (same format the workspace file tree passes to openPreview), so the diff tab
     // is keyed/fetched identically to the tree-driven one.
     void useWorkspacePanelStore.getState().openPreview(sessionId, fileEntry.displayPath, 'diff')
-  }, [sessionId])
+  }, [sessionId, files])
 
   const handleOpenWith = useCallback((event: ReactMouseEvent<HTMLButtonElement>, fileEntry: ChangedFileEntry) => {
     event.stopPropagation()
@@ -81,6 +95,7 @@ export function CurrentTurnChangeCard({
       const ctx = openWithContextForWorkspaceFile(fileEntry.displayPath, fileEntry.apiPath, {
         sessionId,
         serverBaseUrl: getServerBaseUrl(),
+        siblingFiles: files.map((entry) => entry.displayPath),
       })
       const items = buildOpenWithItems(ctx, targets, {
         openInAppBrowser: (url) => useBrowserPanelStore.getState().open(sessionId, url),
@@ -91,7 +106,7 @@ export function CurrentTurnChangeCard({
       })
       setOpenWith({ items, anchor: rect, triggerEl })
     })()
-  }, [openWith, sessionId, t])
+  }, [openWith, sessionId, t, files])
 
   const cardLabel = isLatest
     ? t('chat.turnChangesLatestCardLabel')
@@ -150,7 +165,7 @@ export function CurrentTurnChangeCard({
             <div key={fileEntry.apiPath} className="flex items-center gap-2">
               <button
                 type="button"
-                onClick={() => openDiffInWorkspace(fileEntry)}
+                onClick={() => openChangedFile(fileEntry)}
                 aria-label={t('chat.turnChangesOpenInWorkspaceAria', { path: fileEntry.displayPath })}
                 title={fileEntry.displayPath}
                 className="flex min-h-[52px] min-w-0 flex-1 items-center gap-3 rounded-[var(--radius-md)] px-4 text-left transition-colors hover:bg-[var(--color-surface-hover)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-inset focus-visible:ring-[var(--color-brand)]/35"
diff --git a/desktop/src/components/chat/MessageList.tsx b/desktop/src/components/chat/MessageList.tsx
index a7c467d5..14282d53 100644
--- a/desktop/src/components/chat/MessageList.tsx
+++ b/desktop/src/components/chat/MessageList.tsx
@@ -770,6 +770,40 @@ function buildTurnCardInsertionMap(
   return cardsByRenderIndex
 }
 
+/**
+ * Map each render item to the REAL changed files of the turn it belongs to, so an
+ * assistant message can anchor its output chips on files that were actually
+ * written this turn instead of guessing paths from the prose. Items are attributed
+ * to the most recent preceding non-pending user message (the turn boundary).
+ */
+function buildChangedFilesByRenderIndex(
+  renderItems: RenderItem[],
+  turnChangeCards: TurnChangeCardModel[],
+): Map<number, string[]> {
+  const filesByTurnId = new Map<string, string[]>()
+  for (const card of turnChangeCards) {
+    if (card.checkpoint.code.filesChanged.length > 0) {
+      filesByTurnId.set(card.target.messageId, card.checkpoint.code.filesChanged)
+    }
+  }
+  if (filesByTurnId.size === 0) return new Map()
+
+  const filesByRenderIndex = new Map<number, string[]>()
+  let activeTurnId: string | null = null
+  renderItems.forEach((item, index) => {
+    if (item.kind === 'message' && item.message.type === 'user_text' && !item.message.pending) {
+      activeTurnId = item.message.id
+      return
+    }
+    if (activeTurnId) {
+      const files = filesByTurnId.get(activeTurnId)
+      if (files) filesByRenderIndex.set(index, files)
+    }
+  })
+
+  return filesByRenderIndex
+}
+
 function getApiErrorMessage(error: unknown) {
   return error instanceof ApiError
     ? typeof error.body === 'object' && error.body && 'message' in error.body
@@ -1645,6 +1679,10 @@ export function MessageList({ sessionId, compact = false }: MessageListProps = {
     () => buildTurnCardInsertionMap(renderItems, turnChangeCards),
     [renderItems, turnChangeCards],
   )
+  const changedFilesByRenderIndex = useMemo(
+    () => buildChangedFilesByRenderIndex(renderItems, turnChangeCards),
+    [renderItems, turnChangeCards],
+  )
   const renderItemKeys = useMemo(
     () => renderItems.map(getRenderItemKey),
     [renderItems],
@@ -1903,6 +1941,7 @@ export function MessageList({ sessionId, compact = false }: MessageListProps = {
                 : null
             }
             branchAction={branchActionByMessageId.get(item.message.id)}
+            turnChangedFiles={changedFilesByRenderIndex.get(index)}
           />
         )}
 
@@ -2033,6 +2072,7 @@ export const MessageBlock = memo(function MessageBlock({
   agentTaskNotifications,
   toolResult,
   branchAction,
+  turnChangedFiles,
 }: {
   sessionId?: string | null
   message: UIMessage
@@ -2044,6 +2084,7 @@ export const MessageBlock = memo(function MessageBlock({
     loading?: boolean
     onBranch: () => void
   }
+  turnChangedFiles?: string[]
 }) {
   const t = useTranslation()
 
@@ -2077,6 +2118,7 @@ export const MessageBlock = memo(function MessageBlock({
             branchAction={branchAction}
             sessionId={sessionId ?? undefined}
             timestamp={message.timestamp}
+            turnChangedFiles={turnChangedFiles}
           />
         </SelectableChatMessage>
       )
diff --git a/desktop/src/lib/assistantOutputTargets.test.ts b/desktop/src/lib/assistantOutputTargets.test.ts
index 932fe1c3..bee1250f 100644
--- a/desktop/src/lib/assistantOutputTargets.test.ts
+++ b/desktop/src/lib/assistantOutputTargets.test.ts
@@ -251,3 +251,81 @@ describe('extractAssistantOutputTargets', () => {
     expect(targets.map((target) => target.href)).toEqual(['one.html', 'two.html'])
   })
 })
+
+describe('extractAssistantOutputTargets with changedFiles reconciliation', () => {
+  it('corrects a bare mention to the real changed path in a subfolder', () => {
+    // The reported bug: the model writes /private/tmp/todo-app/index.html but the
+    // prose only says `index.html`, so the chip used to point at the (missing)
+    // workdir-root index.html. With the turn's real changed files it is corrected.
+    const targets = extractAssistantOutputTargets('已创建 `index.html`，直接用浏览器打开。', {
+      workDir: '/private/tmp',
+      changedFiles: [
+        '/private/tmp/todo-app/index.html',
+        '/private/tmp/todo-app/style.css',
+        '/private/tmp/todo-app/app.js',
+      ],
+    })
+
+    expect(targets).toHaveLength(1)
+    expect(targets[0]).toMatchObject({
+      kind: 'local-html',
+      href: 'todo-app/index.html',
+      normalizedPath: 'todo-app/index.html',
+      subtitle: 'todo-app/index.html',
+    })
+  })
+
+  it('drops a mentioned file that the turn never changed', () => {
+    const targets = extractAssistantOutputTargets('参考旧文件 old-report.html 和新结果 result.html', {
+      workDir: '/work',
+      changedFiles: ['/work/out/result.html'],
+    })
+
+    expect(targets.map((target) => target.normalizedPath)).toEqual(['out/result.html'])
+  })
+
+  it('keeps localhost url chips untouched while reconciling files', () => {
+    const targets = extractAssistantOutputTargets('启动后访问 http://localhost:5173/ ，源码见 index.html', {
+      workDir: '/work',
+      changedFiles: ['/work/app/index.html'],
+    })
+
+    const byKind = new Map(targets.map((target) => [target.kind, target]))
+    expect(byKind.get('localhost-url')?.href).toBe('http://localhost:5173/')
+    expect(byKind.get('local-html')?.normalizedPath).toBe('app/index.html')
+  })
+
+  it('rewrites a changed file outside the workdir to its absolute posix path', () => {
+    const targets = extractAssistantOutputTargets('已创建 todo.html', {
+      workDir: 'C:/Users/me/tmp/session',
+      changedFiles: ['D:\\workspace\\demo\\todo.html'],
+    })
+
+    expect(targets).toHaveLength(1)
+    expect(targets[0]).toMatchObject({
+      kind: 'local-html',
+      href: 'D:/workspace/demo/todo.html',
+      normalizedPath: 'D:/workspace/demo/todo.html',
+    })
+  })
+
+  it('falls back to text-only behavior when changedFiles is empty', () => {
+    const targets = extractAssistantOutputTargets('已创建 `index.html`', {
+      workDir: '/private/tmp',
+      changedFiles: [],
+    })
+
+    // No reconciliation → original bare-path behavior (mention kept as-is).
+    expect(targets).toMatchObject([{ kind: 'local-html', normalizedPath: 'index.html' }])
+  })
+
+  it('does not correct when the basename is ambiguous across changed files', () => {
+    const targets = extractAssistantOutputTargets('见 index.html', {
+      workDir: '/work',
+      changedFiles: ['/work/a/index.html', '/work/b/index.html'],
+    })
+
+    // Ambiguous basename match → no unique target, mention dropped rather than guessed.
+    expect(targets).toHaveLength(0)
+  })
+})
diff --git a/desktop/src/lib/assistantOutputTargets.ts b/desktop/src/lib/assistantOutputTargets.ts
index 959d8e1c..30fd4754 100644
--- a/desktop/src/lib/assistantOutputTargets.ts
+++ b/desktop/src/lib/assistantOutputTargets.ts
@@ -24,6 +24,15 @@ export type AssistantOutputTarget = {
 export type ExtractAssistantOutputTargetOptions = {
   workDir?: string | null
   limit?: number
+  /**
+   * The turn's REAL changed files (absolute paths from the turn checkpoint). When
+   * provided, file chips are reconciled against this ground truth: a mentioned
+   * file is corrected to the actual changed path (so `index.html` resolves to the
+   * `todo-app/index.html` that was really written), and a mentioned file that the
+   * turn never changed is dropped instead of pointing at a non-existent path.
+   * Localhost URLs are unaffected. Omitted/empty → fall back to text-only behavior.
+   */
+  changedFiles?: string[]
 }
 
 type FileTargetMatch = {
@@ -217,9 +226,96 @@ export function extractAssistantOutputTargets(
     results.push(candidate.target)
   }
 
+  if (options.changedFiles && options.changedFiles.length > 0) {
+    return reconcileTargetsWithChangedFiles(results, options.changedFiles, workDir)
+  }
+
   return results
 }
 
+/**
+ * Re-anchor file chips onto the turn's real changed files. A mentioned file that
+ * matches a changed file (by exact relative-path suffix, else by basename) is
+ * rewritten to that real path; a mentioned file with no match is dropped so we
+ * never render a chip that opens "file does not exist". Localhost URLs pass
+ * through untouched.
+ */
+function reconcileTargetsWithChangedFiles(
+  targets: AssistantOutputTarget[],
+  changedFiles: string[],
+  workDir: string | null,
+): AssistantOutputTarget[] {
+  const out: AssistantOutputTarget[] = []
+  const seen = new Set<string>()
+
+  for (const target of targets) {
+    if (target.kind === 'localhost-url') {
+      out.push(target)
+      continue
+    }
+
+    const mentioned = target.normalizedPath ?? target.href
+    const match = matchChangedFile(mentioned, changedFiles)
+    if (!match) {
+      continue
+    }
+
+    const resolvedMatch = resolveFilePath(match)
+    const corrected = workDir && isWithinWorkDir(resolvedMatch, workDir)
+      ? relativeFilePath(workDir, resolvedMatch)
+      : toPosixPath(match)
+
+    const key = `${target.kind}:${corrected}`
+    if (seen.has(key)) {
+      continue
+    }
+    seen.add(key)
+
+    out.push({
+      ...target,
+      href: corrected,
+      normalizedPath: corrected,
+      subtitle: corrected,
+    })
+  }
+
+  return out
+}
+
+/**
+ * Resolve a mentioned (often relative or bare) path against the turn's absolute
+ * changed-file list. Prefer an unambiguous relative-suffix match, then fall back
+ * to an unambiguous basename match. Ambiguous matches return null (we'd rather
+ * keep the original text path than guess wrong).
+ */
+function matchChangedFile(mentioned: string, changedFiles: string[]): string | null {
+  const normalized = toPosixPath(mentioned).replace(/^\.?\//, '').toLowerCase()
+  if (!normalized) {
+    return null
+  }
+  const basename = normalized.split('/').pop() ?? normalized
+
+  const suffixMatches = changedFiles.filter((file) => {
+    const normalizedFile = toPosixPath(file).toLowerCase()
+    return normalizedFile === normalized || normalizedFile.endsWith(`/${normalized}`)
+  })
+  if (suffixMatches.length === 1) {
+    return suffixMatches[0]!
+  }
+  if (suffixMatches.length > 1) {
+    return null
+  }
+
+  const basenameMatches = changedFiles.filter(
+    (file) => getBasename(file).toLowerCase() === basename,
+  )
+  if (basenameMatches.length === 1) {
+    return basenameMatches[0]!
+  }
+
+  return null
+}
+
 function toWorkspaceFileTarget(candidate: string, workDir: string | null): FileTargetMatch | null {
   if (!candidate || candidate.startsWith('file://') || isExternalUrl(candidate)) {
     return null
diff --git a/desktop/src/lib/handlePreviewLink.test.ts b/desktop/src/lib/handlePreviewLink.test.ts
index 46c25f2a..e53d84a2 100644
--- a/desktop/src/lib/handlePreviewLink.test.ts
+++ b/desktop/src/lib/handlePreviewLink.test.ts
@@ -75,12 +75,18 @@ describe('handlePreviewLink', () => {
     expect(deps.openFilePreview).not.toHaveBeenCalled()
   })
 
-  it('routes a frontend project index.html to workspace preview instead of static browser preview', () => {
+  it('routes a hand-authored single-page index.html to the static browser preview', () => {
+    // Without change-set context a bare index.html is assumed to be a standalone
+    // static page (the common "make me a todo page" output), so it renders in the
+    // in-app browser rather than dropping the user into the source view.
     const deps = makeDeps()
     const handled = handlePreviewLink('todo-app/index.html', deps)
     expect(handled).toBe(true)
-    expect(deps.openFilePreview).toHaveBeenCalledWith('s1', 'todo-app/index.html')
-    expect(deps.openBrowser).not.toHaveBeenCalled()
+    expect(deps.openBrowser).toHaveBeenCalledWith(
+      's1',
+      'http://127.0.0.1:8787/preview-fs/s1/todo-app/index.html',
+    )
+    expect(deps.openFilePreview).not.toHaveBeenCalled()
   })
 
   it('routes relative previewable docs to openFilePreview with the relative path', () => {
diff --git a/desktop/src/lib/htmlPreviewPolicy.test.ts b/desktop/src/lib/htmlPreviewPolicy.test.ts
new file mode 100644
index 00000000..94e738b1
--- /dev/null
+++ b/desktop/src/lib/htmlPreviewPolicy.test.ts
@@ -0,0 +1,82 @@
+import { describe, expect, it } from 'vitest'
+import { isHtmlFilePath, shouldOfferStaticHtmlPreview } from './htmlPreviewPolicy'
+
+describe('isHtmlFilePath', () => {
+  it('matches html/htm/xhtml regardless of separators and suffixes', () => {
+    expect(isHtmlFilePath('index.html')).toBe(true)
+    expect(isHtmlFilePath('page.htm')).toBe(true)
+    expect(isHtmlFilePath('a/b.xhtml')).toBe(true)
+    expect(isHtmlFilePath('C:\\proj\\page.html')).toBe(true)
+    expect(isHtmlFilePath('app.html?v=2#top')).toBe(true)
+  })
+
+  it('rejects non-html paths', () => {
+    expect(isHtmlFilePath('style.css')).toBe(false)
+    expect(isHtmlFilePath('readme.md')).toBe(false)
+  })
+})
+
+describe('shouldOfferStaticHtmlPreview', () => {
+  it('is false for non-html files', () => {
+    expect(shouldOfferStaticHtmlPreview('app.js')).toBe(false)
+    expect(shouldOfferStaticHtmlPreview('styles/site.css')).toBe(false)
+  })
+
+  it('offers static preview for non-index html pages', () => {
+    expect(shouldOfferStaticHtmlPreview('todo.html')).toBe(true)
+    expect(shouldOfferStaticHtmlPreview('pages/about.html')).toBe(true)
+  })
+
+  it('offers static preview for a hand-authored single-page index.html (no project manifest)', () => {
+    // The real-world regression: a "make me a todo page" output written into a
+    // subfolder must still get a browser preview — it is NOT a build template.
+    expect(shouldOfferStaticHtmlPreview('todo-app/index.html')).toBe(true)
+    expect(
+      shouldOfferStaticHtmlPreview('todo-app/index.html', {
+        siblingFiles: ['todo-app/index.html', 'todo-app/style.css', 'todo-app/app.js'],
+      }),
+    ).toBe(true)
+  })
+
+  it('defaults a bare index.html to static preview when no change-set context is given', () => {
+    expect(shouldOfferStaticHtmlPreview('index.html')).toBe(true)
+  })
+
+  it('routes a framework-template index.html (manifest in the same change-set) to source view', () => {
+    expect(
+      shouldOfferStaticHtmlPreview('index.html', {
+        siblingFiles: ['index.html', 'package.json', 'vite.config.ts', 'src/main.tsx'],
+      }),
+    ).toBe(false)
+    expect(
+      shouldOfferStaticHtmlPreview('my-app/index.html', {
+        siblingFiles: ['my-app/package.json', 'my-app/index.html', 'my-app/src/main.tsx'],
+      }),
+    ).toBe(false)
+  })
+
+  it('only treats a manifest as a signal when it sits at or above the index.html dir', () => {
+    // A package.json in an unrelated sibling folder must not suppress the preview.
+    expect(
+      shouldOfferStaticHtmlPreview('site/index.html', {
+        siblingFiles: ['api/package.json', 'site/index.html', 'site/app.js'],
+      }),
+    ).toBe(true)
+  })
+
+  it('always offers static preview for build-output and generated exports', () => {
+    expect(shouldOfferStaticHtmlPreview('dist/index.html')).toBe(true)
+    expect(shouldOfferStaticHtmlPreview('out/index.html')).toBe(true)
+    expect(shouldOfferStaticHtmlPreview('build/index.html')).toBe(true)
+    expect(shouldOfferStaticHtmlPreview('report_files/index.html')).toBe(true)
+    // Even with a manifest present, a built artifact dir stays statically previewable.
+    expect(
+      shouldOfferStaticHtmlPreview('dist/index.html', { siblingFiles: ['package.json', 'dist/index.html'] }),
+    ).toBe(true)
+  })
+
+  it('normalizes windows separators and url suffixes', () => {
+    expect(shouldOfferStaticHtmlPreview('todo-app\\index.html')).toBe(true)
+    expect(shouldOfferStaticHtmlPreview('page.html?v=1#frag')).toBe(true)
+  })
+})
diff --git a/desktop/src/lib/htmlPreviewPolicy.ts b/desktop/src/lib/htmlPreviewPolicy.ts
index 773b5741..dd0b0534 100644
--- a/desktop/src/lib/htmlPreviewPolicy.ts
+++ b/desktop/src/lib/htmlPreviewPolicy.ts
@@ -14,6 +14,21 @@ const STATIC_OUTPUT_DIRS = new Set([
   'storybook-static',
 ])
 
+/**
+ * Files whose presence in the SAME change-set marks a buildable source project
+ * (a framework scaffold). For such a project a root `index.html` is almost
+ * always a build-tool template (`<script type="module" src="/src/main.tsx">`)
+ * that renders blank when served statically — it needs a dev server — so we
+ * route it to the workspace source view instead of a static browser preview.
+ *
+ * A hand-authored single-page `index.html` (the common "make me a todo page"
+ * output) ships with no manifest alongside it, so it stays statically
+ * previewable. This is the signal that lets us tell the two apart without
+ * reading file contents.
+ */
+const PROJECT_MANIFEST_RE =
+  /^(?:package\.json|(?:vite|next|nuxt|svelte|astro|remix|rollup|webpack|rsbuild|rspack|parcel|gatsby)\.config\.[cm]?[jt]s|angular\.json|deno\.jsonc?)$/i
+
 function normalizePathForPolicy(filePath: string): string {
   return filePath
     .split(/[?#]/, 1)[0]!
@@ -25,14 +40,61 @@ export function isHtmlFilePath(filePath: string): boolean {
   return HTML_EXT.test(normalizePathForPolicy(filePath))
 }
 
-export function shouldOfferStaticHtmlPreview(filePath: string): boolean {
+function dirOfNormalized(normalizedPath: string): string {
+  const slash = normalizedPath.lastIndexOf('/')
+  return slash < 0 ? '' : normalizedPath.slice(0, slash)
+}
+
+/** True when `ancestorDir` is the same as, or a parent of, `dir`. */
+function isAtOrAbove(ancestorDir: string, dir: string): boolean {
+  if (ancestorDir === dir) return true
+  return ancestorDir === '' || dir.startsWith(`${ancestorDir}/`)
+}
+
+/**
+ * True when the change-set contains a project manifest sitting at or above the
+ * `index.html`'s own directory — i.e. the html is the entry template of a real
+ * buildable project rather than a standalone static page.
+ */
+function hasProjectManifestSibling(indexNormalizedPath: string, siblingFiles: string[]): boolean {
+  const indexDir = dirOfNormalized(indexNormalizedPath)
+  return siblingFiles.some((raw) => {
+    const sibling = normalizePathForPolicy(raw)
+    const name = sibling.slice(sibling.lastIndexOf('/') + 1)
+    if (!PROJECT_MANIFEST_RE.test(name)) return false
+    return isAtOrAbove(dirOfNormalized(sibling), indexDir)
+  })
+}
+
+/**
+ * Decide whether an html file should be offered as a static browser preview
+ * (served as-is via `/preview-fs` or `/local-file`) versus the workspace source
+ * view.
+ *
+ * Everything that is clearly a finished static artifact previews statically:
+ * non-`index` pages (`todo.html`), generated `*_files/index.html` exports, and
+ * anything under a build-output dir (`dist/`, `build/`, `out/`, …).
+ *
+ * A bare `index.html` is ambiguous from its path alone. When the caller can
+ * supply the rest of the change-set via `opts.siblingFiles`, we treat the html
+ * as a framework template (→ source view, not static preview) ONLY when a
+ * project manifest (`package.json`, `vite.config.*`, …) accompanies it. Without
+ * that signal we default to offering the static preview, so a hand-authored
+ * single-page `index.html` is no longer mis-classified as a build template.
+ */
+export function shouldOfferStaticHtmlPreview(
+  filePath: string,
+  opts?: { siblingFiles?: string[] },
+): boolean {
   const normalized = normalizePathForPolicy(filePath)
   if (!HTML_EXT.test(normalized)) return false
-  if (!INDEX_HTML_RE.test(normalized)) return true
   if (GENERATED_STATIC_FILES_DIR_RE.test(normalized)) return true
-
-  return normalized
-    .split('/')
-    .filter(Boolean)
-    .some((segment) => STATIC_OUTPUT_DIRS.has(segment.toLowerCase()))
+  if (normalized.split('/').filter(Boolean).some((segment) => STATIC_OUTPUT_DIRS.has(segment.toLowerCase()))) {
+    return true
+  }
+  if (!INDEX_HTML_RE.test(normalized)) return true
+  if (opts?.siblingFiles && hasProjectManifestSibling(normalized, opts.siblingFiles)) {
+    return false
+  }
+  return true
 }
diff --git a/desktop/src/lib/openWithContextForHref.test.ts b/desktop/src/lib/openWithContextForHref.test.ts
index 31099e4f..21e276ff 100644
--- a/desktop/src/lib/openWithContextForHref.test.ts
+++ b/desktop/src/lib/openWithContextForHref.test.ts
@@ -77,13 +77,32 @@ describe('openWithContextForWorkspaceFile', () => {
     expect(result).toEqual({ kind: 'file', absolutePath: '/w/proj/README.md', relPath: 'README.md', previewable: true })
   })
 
-  it('frontend project index.html rel path → no inAppBrowserUrl because it needs a dev server', () => {
-    const result = openWithContextForWorkspaceFile('todo-app/index.html', '/w/proj/todo-app/index.html', { sessionId: SESSION, serverBaseUrl: BASE })
+  it('hand-authored single-page index.html (no manifest in change-set) → static preview offered', () => {
+    const result = openWithContextForWorkspaceFile('todo-app/index.html', '/w/proj/todo-app/index.html', {
+      sessionId: SESSION,
+      serverBaseUrl: BASE,
+      siblingFiles: ['todo-app/index.html', 'todo-app/style.css', 'todo-app/app.js'],
+    })
     expect(result).toEqual({
       kind: 'file',
       absolutePath: '/w/proj/todo-app/index.html',
       relPath: 'todo-app/index.html',
       previewable: true,
+      inAppBrowserUrl: previewFsUrl(BASE, SESSION, 'todo-app/index.html'),
+    })
+  })
+
+  it('framework-template index.html (manifest in change-set) → no inAppBrowserUrl (needs dev server)', () => {
+    const result = openWithContextForWorkspaceFile('index.html', '/w/proj/index.html', {
+      sessionId: SESSION,
+      serverBaseUrl: BASE,
+      siblingFiles: ['index.html', 'package.json', 'vite.config.ts', 'src/main.tsx'],
+    })
+    expect(result).toEqual({
+      kind: 'file',
+      absolutePath: '/w/proj/index.html',
+      relPath: 'index.html',
+      previewable: true,
     })
   })
 
@@ -126,4 +145,31 @@ describe('openWithContextForWorkspaceFile', () => {
       expect(result.previewable).toBe(true)
     }
   })
+
+  it('outside-workspace html (absolute displayPath) → inAppBrowserUrl via localFileUrl, not preview-fs', () => {
+    // A changed file that could not be relativized arrives with an absolute relPath;
+    // it lives outside the workdir, so it must be served by the /local-file route.
+    const result = openWithContextForWorkspaceFile('D:/workspace/demo/todo.html', 'D:\\workspace\\demo\\todo.html', {
+      sessionId: SESSION,
+      serverBaseUrl: BASE,
+    })
+    expect(result).toEqual({
+      kind: 'file',
+      absolutePath: 'D:\\workspace\\demo\\todo.html',
+      relPath: 'D:/workspace/demo/todo.html',
+      previewable: true,
+      inAppBrowserUrl: localFileUrl(BASE, 'D:\\workspace\\demo\\todo.html'),
+    })
+  })
+
+  it('outside-workspace POSIX html absolute path → inAppBrowserUrl via localFileUrl', () => {
+    const result = openWithContextForWorkspaceFile('/elsewhere/site/todo.html', '/elsewhere/site/todo.html', {
+      sessionId: SESSION,
+      serverBaseUrl: BASE,
+    })
+    expect(result.kind).toBe('file')
+    if (result.kind === 'file') {
+      expect(result.inAppBrowserUrl).toBe(localFileUrl(BASE, '/elsewhere/site/todo.html'))
+    }
+  })
 })
diff --git a/desktop/src/lib/openWithContextForHref.ts b/desktop/src/lib/openWithContextForHref.ts
index 3dce9eeb..2267e1e8 100644
--- a/desktop/src/lib/openWithContextForHref.ts
+++ b/desktop/src/lib/openWithContextForHref.ts
@@ -3,18 +3,36 @@ import { shouldOfferStaticHtmlPreview } from './htmlPreviewPolicy'
 import { isAbsoluteLocalPath, localFileUrl, previewFsUrl } from './handlePreviewLink'
 import type { OpenWithContext } from './openWithItems'
 
-/** Build an open-with context for a workspace file (we have both its relative + absolute path). */
+/**
+ * Build an open-with context for a workspace file (we have both its relative +
+ * absolute path).
+ *
+ * `siblingFiles` is the rest of the same change-set (the turn's changed files).
+ * It lets {@link shouldOfferStaticHtmlPreview} tell a hand-authored single-page
+ * `index.html` (→ offer a static browser preview) from a framework template
+ * that ships with a `package.json` / `vite.config.*` (→ source view only).
+ */
 export function openWithContextForWorkspaceFile(
   relPath: string,
   absolutePath: string,
-  opts: { sessionId: string; serverBaseUrl: string },
+  opts: { sessionId: string; serverBaseUrl: string; siblingFiles?: string[] },
 ): OpenWithContext {
+  // A changed file that could not be relativized against the workdir arrives with
+  // an absolute `relPath` — it lives outside the session workspace (e.g. another
+  // drive). Such a file is served by the $HOME/registered-root /local-file route,
+  // not the workdir-sandboxed /preview-fs route.
+  const outsideWorkspace = isAbsoluteLocalPath(relPath)
+  const inAppBrowserUrl = shouldOfferStaticHtmlPreview(relPath, { siblingFiles: opts.siblingFiles })
+    ? outsideWorkspace
+      ? localFileUrl(opts.serverBaseUrl, absolutePath)
+      : previewFsUrl(opts.serverBaseUrl, opts.sessionId, relPath)
+    : undefined
   return {
     kind: 'file',
     absolutePath,
     relPath,
     previewable: true,
-    inAppBrowserUrl: shouldOfferStaticHtmlPreview(relPath) ? previewFsUrl(opts.serverBaseUrl, opts.sessionId, relPath) : undefined,
+    inAppBrowserUrl,
   }
 }
 
diff --git a/desktop/src/stores/chatStore.test.ts b/desktop/src/stores/chatStore.test.ts
index b7d817e5..d6a48202 100644
--- a/desktop/src/stores/chatStore.test.ts
+++ b/desktop/src/stores/chatStore.test.ts
@@ -129,6 +129,7 @@ import { sessionsApi } from '../api/sessions'
 import {
   mapHistoryMessagesToUiMessages,
   reconstructAgentNotifications,
+  stripGeneratedImageMetadataLines,
   type PerSessionState,
   useChatStore,
 } from './chatStore'
@@ -163,6 +164,28 @@ function makeSession(overrides: Partial<PerSessionState> = {}): PerSessionState
   }
 }
 
+describe('stripGeneratedImageMetadataLines', () => {
+  it('removes simple, detailed, and resize metadata lines but keeps the prompt body', () => {
+    const text = [
+      'first line of the prompt',
+      'second line',
+      '[Image source: C:\\Users\\Relakkes\\.claude\\uploads\\sid\\a.png]',
+      '[Image: source: /Users/me/.claude/uploads/sid/b.png, original 1024x768, displayed at 512x384. Multiply coordinates by 2 to map to original image.]',
+      '[Image: original 800x600, displayed at 400x300. Multiply coordinates by 2 to map to original image.]',
+    ].join('\n')
+    expect(stripGeneratedImageMetadataLines(text)).toBe('first line of the prompt\nsecond line')
+  })
+
+  it('normalizes CRLF and leaves metadata-free text untouched', () => {
+    expect(stripGeneratedImageMetadataLines('a\r\nb\r\n')).toBe('a\nb')
+    expect(stripGeneratedImageMetadataLines('just a normal prompt')).toBe('just a normal prompt')
+  })
+
+  it('returns empty string when the text is only metadata', () => {
+    expect(stripGeneratedImageMetadataLines('[Image source: /tmp/x.png]')).toBe('')
+  })
+})
+
 describe('chatStore history mapping', () => {
   beforeEach(() => {
     sendMock.mockReset()
@@ -3522,6 +3545,64 @@ describe('chatStore history mapping', () => {
     ])
   })
 
+  it('does not leak an image-bearing prompt when the replay appends [Image source] metadata (Windows path)', () => {
+    // The optimistic message (e.g. a visual-selection annotation card) stores the
+    // prompt body in modelContent with a hidden display. The CLI replay carries
+    // the server-appended `[Image source: …]` line on the same text. Dedupe must
+    // still match — otherwise the raw prompt + absolute upload path leak in as a
+    // second grey bubble (the reported Windows regression).
+    const prompt = '请根据截图中编号 1 的蓝色标注修改本地前端。\n目标元素：<button>'
+    useChatStore.setState({
+      sessions: {
+        [TEST_SESSION_ID]: makeSession({
+          messages: [
+            {
+              id: 'live-user',
+              type: 'user_text',
+              content: '',
+              modelContent: prompt,
+              timestamp: 1,
+            },
+          ],
+          chatState: 'thinking',
+        }),
+      },
+    })
+
+    useChatStore.getState().handleServerMessage(TEST_SESSION_ID, {
+      type: 'user_message_replay',
+      content: `${prompt}\n[Image source: C:\\Users\\Relakkes\\.claude\\uploads\\sid\\82017405-_button_.png]`,
+    })
+
+    const userMessages = useChatStore.getState().sessions[TEST_SESSION_ID]?.messages
+      .filter((message) => message.type === 'user_text')
+    expect(userMessages).toHaveLength(1)
+    expect(userMessages?.[0]).toMatchObject({ content: '', modelContent: prompt })
+  })
+
+  it('dedupes an image-bearing prompt when the replay appends detailed (macOS) image metadata', () => {
+    const prompt = 'describe this screenshot for me'
+    useChatStore.setState({
+      sessions: {
+        [TEST_SESSION_ID]: makeSession({
+          messages: [
+            { id: 'live-user', type: 'user_text', content: prompt, timestamp: 1 },
+          ],
+          chatState: 'thinking',
+        }),
+      },
+    })
+
+    useChatStore.getState().handleServerMessage(TEST_SESSION_ID, {
+      type: 'user_message_replay',
+      content: `${prompt}\n[Image: source: /Users/me/.claude/uploads/sid/a.png, original 1024x768, displayed at 512x384. Multiply coordinates by 2 to map to original image.]`,
+    })
+
+    const userMessages = useChatStore.getState().sessions[TEST_SESSION_ID]?.messages
+      .filter((message) => message.type === 'user_text')
+    expect(userMessages).toHaveLength(1)
+  })
+
   it('flushes pending text before appending an error message', () => {
     vi.useFakeTimers()
 
diff --git a/desktop/src/stores/chatStore.ts b/desktop/src/stores/chatStore.ts
index 143b0227..0edf7c8c 100644
--- a/desktop/src/stores/chatStore.ts
+++ b/desktop/src/stores/chatStore.ts
@@ -2188,6 +2188,24 @@ function isGeneratedImageMetadataText(text: string): boolean {
   return Boolean(extractImageMetadataSourcePath(text)) || IMAGE_RESIZE_METADATA_RE.test(text.trim())
 }
 
+/**
+ * Strip the generated image-metadata lines (`[Image source: …]`, resize notes)
+ * that the server appends to a user turn's text. The optimistic message never
+ * carried them, so live-replay dedupe must normalize them away first — otherwise
+ * `findCurrentTurnUserMessageIndex` never matches and the raw prompt leaks in as
+ * a duplicate bubble. This was most visible on Windows, where the appended
+ * absolute upload path (`[Image source: C:\Users\…\uploads\…png]`) made the
+ * mismatch obvious, but it affects any message that carries an image.
+ */
+export function stripGeneratedImageMetadataLines(text: string): string {
+  return text
+    .replace(/\r\n?/g, '\n')
+    .split('\n')
+    .filter((line) => !isGeneratedImageMetadataText(line))
+    .join('\n')
+    .trim()
+}
+
 function parseVisualSelectionHistoryPrompt(text: string): VisualSelectionHistoryDisplay | null {
   const lines = text.replace(/\r\n?/g, '\n').split('\n')
   if (lines[0]?.trim() !== VISUAL_SELECTION_PROMPT_HEADER) return null
@@ -2745,16 +2763,21 @@ function extractLeadingFileReferences(text: string): {
   }
 }
 
-function appendReplayedUserMessage(
+export function appendReplayedUserMessage(
   messages: UIMessage[],
   content: string,
   timestamp: number,
 ): UIMessage[] {
-  const parsed = extractLeadingFileReferences(content)
-  const displayContent = parsed.content.trim() || content.trim()
+  // The replayed text carries server-appended image-metadata lines that the
+  // optimistic message never had. Normalize them away (same as the history
+  // mapping) so the dedupe below can match the already-rendered message instead
+  // of appending the raw prompt — paths and all — as a duplicate bubble.
+  const sanitized = stripGeneratedImageMetadataLines(content) || content.trim()
+  const parsed = extractLeadingFileReferences(sanitized)
+  const displayContent = parsed.content.trim() || sanitized
   if (!displayContent) return messages
 
-  const modelContent = parsed.modelContent ?? content.trim()
+  const modelContent = parsed.modelContent ?? sanitized
   const currentTurnUserIndex = findCurrentTurnUserMessageIndex(messages, modelContent)
   if (currentTurnUserIndex >= 0) {
     const optimisticMessage = messages[currentTurnUserIndex]
diff --git a/src/server/__tests__/workspace-service.test.ts b/src/server/__tests__/workspace-service.test.ts
index 203005de..8ac31c59 100644
--- a/src/server/__tests__/workspace-service.test.ts
+++ b/src/server/__tests__/workspace-service.test.ts
@@ -4,6 +4,10 @@ import { execFileSync } from 'node:child_process'
 import * as os from 'node:os'
 import * as path from 'node:path'
 import { WorkspaceService } from '../services/workspaceService.js'
+import {
+  clearFilesystemAccessRootsForTests,
+  registerFilesystemAccessRoot,
+} from '../services/filesystemAccessRoots.js'
 
 const cleanupDirs = new Set<string>()
 const ONE_MIB = 1024 * 1024
@@ -76,6 +80,43 @@ afterEach(async () => {
   cleanupDirs.clear()
 })
 
+describe('WorkspaceService outside-workspace preview', () => {
+  afterEach(() => {
+    clearFilesystemAccessRootsForTests()
+  })
+
+  it('rejects a file outside the workdir until its dir is a registered access root, then reads it', async () => {
+    const workDir = await makeTempDir('workspace-service-work-')
+    const outsideDir = await makeTempDir('workspace-service-outside-')
+    const outsideFile = path.join(outsideDir, 'todo.html')
+    await fs.writeFile(outsideFile, '<h1>hi</h1>\n')
+
+    const service = new WorkspaceService(async (sessionId) => sessionId === 'session-1' ? workDir : null)
+
+    // Not registered yet → treated as a sandbox escape.
+    await expect(service.readFile('session-1', outsideFile)).rejects.toThrow(/outside workspace/)
+
+    // Registered (as the turn-checkpoint flow does for changed files) → readable.
+    registerFilesystemAccessRoot(outsideDir)
+    const allowed = await service.readFile('session-1', outsideFile)
+    expect(allowed.state).toBe('ok')
+    expect(allowed.content).toContain('<h1>hi</h1>')
+  })
+
+  it('still rejects an unrelated path even when another outside dir is registered', async () => {
+    const workDir = await makeTempDir('workspace-service-work-')
+    const registeredDir = await makeTempDir('workspace-service-reg-')
+    const unrelatedDir = await makeTempDir('workspace-service-unrelated-')
+    const unrelatedFile = path.join(unrelatedDir, 'secret.txt')
+    await fs.writeFile(unrelatedFile, 'nope\n')
+    registerFilesystemAccessRoot(registeredDir)
+
+    const service = new WorkspaceService(async (sessionId) => sessionId === 'session-1' ? workDir : null)
+
+    await expect(service.readFile('session-1', unrelatedFile)).rejects.toThrow(/outside workspace/)
+  })
+})
+
 describe('WorkspaceService', () => {
   it('returns git status for modified, added, deleted, and untracked files', async () => {
     const repoDir = await createGitWorkspace()
diff --git a/src/server/api/sessions.ts b/src/server/api/sessions.ts
index e26de811..33fc73b0 100644
--- a/src/server/api/sessions.ts
+++ b/src/server/api/sessions.ts
@@ -40,7 +40,7 @@ import {
   createSessionBranch,
   SessionBranchingError,
 } from '../../utils/sessionBranching.js'
-import { registerFilesystemAccessRoot } from '../services/filesystemAccessRoots.js'
+import { registerChangedFileAccessRoot, registerFilesystemAccessRoot } from '../services/filesystemAccessRoots.js'
 import { traceCaptureService, trimTraceCallPreviews } from '../services/traceCaptureService.js'
 
 const workspaceService = new WorkspaceService(
@@ -851,6 +851,14 @@ async function branchSession(req: Request, sessionId: string): Promise<Response>
 
 async function getTurnCheckpoints(sessionId: string): Promise<Response> {
   const checkpoints = await listSessionTurnCheckpoints(sessionId)
+  // Make this turn's real changed files previewable even when they live outside
+  // the session workdir (e.g. the user told the model to write to an absolute
+  // path on another drive). Writing them was authorized, so previewing is too.
+  for (const checkpoint of checkpoints) {
+    for (const filePath of checkpoint.code.filesChanged) {
+      registerChangedFileAccessRoot(filePath, checkpoint.workDir)
+    }
+  }
   return Response.json({ checkpoints })
 }
 
diff --git a/src/server/services/filesystemAccessRoots.test.ts b/src/server/services/filesystemAccessRoots.test.ts
new file mode 100644
index 00000000..0f19bb7d
--- /dev/null
+++ b/src/server/services/filesystemAccessRoots.test.ts
@@ -0,0 +1,37 @@
+import { afterEach, beforeEach, describe, expect, it } from 'bun:test'
+import {
+  clearFilesystemAccessRootsForTests,
+  isWithinRegisteredFilesystemRoot,
+  registerChangedFileAccessRoot,
+} from './filesystemAccessRoots.js'
+
+describe('registerChangedFileAccessRoot', () => {
+  beforeEach(() => clearFilesystemAccessRootsForTests())
+  afterEach(() => clearFilesystemAccessRootsForTests())
+
+  it('registers the containing dir of a changed file outside the workdir', () => {
+    registerChangedFileAccessRoot('/elsewhere/proj/todo.html', '/work/dir')
+    expect(isWithinRegisteredFilesystemRoot('/elsewhere/proj/todo.html')).toBe(true)
+    // sibling assets in the same dir become previewable too (html needs its css/js)
+    expect(isWithinRegisteredFilesystemRoot('/elsewhere/proj/style.css')).toBe(true)
+    // an unrelated dir stays denied
+    expect(isWithinRegisteredFilesystemRoot('/elsewhere/other/secret.txt')).toBe(false)
+  })
+
+  it('skips files already inside the workdir (already previewable)', () => {
+    registerChangedFileAccessRoot('/work/dir/sub/page.html', '/work/dir')
+    expect(isWithinRegisteredFilesystemRoot('/work/dir/sub/page.html')).toBe(false)
+  })
+
+  it('registers when no workdir context is given', () => {
+    registerChangedFileAccessRoot('/scratch/a/b.html', null)
+    expect(isWithinRegisteredFilesystemRoot('/scratch/a/b.html')).toBe(true)
+  })
+
+  it('ignores empty / nullish input', () => {
+    registerChangedFileAccessRoot('', '/work/dir')
+    registerChangedFileAccessRoot(null, '/work/dir')
+    registerChangedFileAccessRoot(undefined, '/work/dir')
+    expect(isWithinRegisteredFilesystemRoot('/anything')).toBe(false)
+  })
+})
diff --git a/src/server/services/filesystemAccessRoots.ts b/src/server/services/filesystemAccessRoots.ts
index 0b3aeb5a..c0d38285 100644
--- a/src/server/services/filesystemAccessRoots.ts
+++ b/src/server/services/filesystemAccessRoots.ts
@@ -15,6 +15,28 @@ export function registerFilesystemAccessRoot(rootPath: string | null | undefined
   registeredRoots.add(path.resolve(normalizeDriveRootPathForPlatform(rootPath)))
 }
 
+/**
+ * Register the directory of a file this session actually changed so it becomes
+ * previewable, even when the user pointed the model at an absolute path outside
+ * the session workdir (a different folder, or a different drive on Windows).
+ *
+ * Writing the file was already authorized via the permission system, so reading
+ * it back for a preview is consistent. Files inside the workdir need nothing —
+ * they are previewable already — so those are skipped to keep the root set tight.
+ */
+export function registerChangedFileAccessRoot(
+  absoluteFilePath: string | null | undefined,
+  workDir: string | null | undefined,
+): void {
+  if (!absoluteFilePath) return
+  const resolved = path.resolve(normalizeDriveRootPathForPlatform(absoluteFilePath))
+  if (workDir) {
+    const root = path.resolve(normalizeDriveRootPathForPlatform(workDir))
+    if (isWithinRoot(resolved, root)) return
+  }
+  registeredRoots.add(path.dirname(resolved))
+}
+
 export function isWithinRegisteredFilesystemRoot(targetPath: string): boolean {
   for (const rootPath of registeredRoots) {
     if (isWithinRoot(targetPath, rootPath)) return true
diff --git a/src/server/services/workspaceService.ts b/src/server/services/workspaceService.ts
index 196bd14f..8e339e37 100644
--- a/src/server/services/workspaceService.ts
+++ b/src/server/services/workspaceService.ts
@@ -6,6 +6,7 @@ import { diffLines } from 'diff'
 import type { MessageEntry } from './sessionService.js'
 import type { FileHistorySnapshot } from '../../utils/fileHistory.js'
 import { getClaudeConfigHomeDir } from '../../utils/envUtils.js'
+import { isWithinRegisteredFilesystemRoot } from './filesystemAccessRoots.js'
 import {
   isSameOrInsidePathForPlatform,
   normalizeDriveRootPathForPlatform,
@@ -1059,6 +1060,14 @@ export class WorkspaceService {
 
     const absolutePath = path.resolve(workDir, requestedPath || '.')
     if (!this.isWithinRoot(absolutePath, workDir)) {
+      // Files this session changed outside its workdir (the user pointed the
+      // model at an absolute path elsewhere, possibly another drive) are
+      // registered as access roots when the turn checkpoint is built. Preview
+      // those by absolute path — they have no workspace-relative form — instead
+      // of rejecting them as out-of-sandbox.
+      if (isWithinRegisteredFilesystemRoot(absolutePath)) {
+        return this.resolveOutsideWorkspacePath(absolutePath, requestedPath)
+      }
       throw new Error(`Path is outside workspace: ${requestedPath}`)
     }
 
@@ -1080,6 +1089,33 @@ export class WorkspaceService {
     }
   }
 
+  /**
+   * Resolve a path that sits OUTSIDE the session workdir but inside a registered
+   * access root (a file this turn actually changed elsewhere). Such a file has no
+   * meaningful workspace-relative form, so it is keyed by its absolute request
+   * path and rooted at its own containing directory — enough for `readFile`
+   * (and a best-effort git diff if that directory happens to be a repo).
+   */
+  private async resolveOutsideWorkspacePath(
+    absolutePath: string,
+    requestedPath: string,
+  ): Promise<WorkspacePathResolution> {
+    let canonicalTargetPath = absolutePath
+    try {
+      canonicalTargetPath = await fs.realpath(absolutePath)
+    } catch {
+      // File may not exist yet, or realpath is unavailable — keep the raw path.
+    }
+    return {
+      absolutePath,
+      requestedPath,
+      workspaceRoot: path.dirname(absolutePath),
+      canonicalWorkspaceRoot: path.dirname(canonicalTargetPath),
+      canonicalTargetPath,
+      relativePath: this.normalizeRequestedPath(requestedPath),
+    }
+  }
+
   private async validateCanonicalWorkspacePath(
     canonicalWorkspaceRoot: string,
     absolutePath: string,