diff --git a/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx b/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
index 40e69906..d43ebffc 100644
--- a/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
+++ b/desktop/src/components/chat/AssistantOutputTargetCard.test.tsx
@@ -93,12 +93,9 @@ describe('AssistantOutputTargetCard', () => {
     expect(openBrowser).toHaveBeenCalledWith('s1', 'http://localhost:5173/')
   })
 
-  it('copies the normalized path when Copy is clicked', () => {
-    const writeText = vi.fn().mockResolvedValue(undefined)
-    Object.assign(navigator, { clipboard: { writeText } })
+  it('does not render a copy button for output target cards', () => {
     render(<AssistantOutputTargetCard target={markdownTarget} sessionId="s1" />)
-    fireEvent.click(screen.getByLabelText('assistantOutputs.copy'))
-    expect(writeText).toHaveBeenCalledWith('docs/readme.md')
+    expect(screen.queryByLabelText('assistantOutputs.copy')).not.toBeInTheDocument()
   })
 
   it('opens the open-with menu with URL items for a localhost target', async () => {
diff --git a/desktop/src/components/chat/AssistantOutputTargetCard.tsx b/desktop/src/components/chat/AssistantOutputTargetCard.tsx
index 8ddca096..83413cf1 100644
--- a/desktop/src/components/chat/AssistantOutputTargetCard.tsx
+++ b/desktop/src/components/chat/AssistantOutputTargetCard.tsx
@@ -1,6 +1,6 @@
 import { useCallback, useState } from 'react'
 import type { MouseEvent as ReactMouseEvent } from 'react'
-import { ChevronDown, Copy, ExternalLink, Globe } from 'lucide-react'
+import { ChevronDown, ExternalLink, Globe } from 'lucide-react'
 import type { AssistantOutputTarget } from '../../lib/assistantOutputTargets'
 import { useTranslation, type TranslationKey } from '../../i18n'
 import { OpenWithMenu } from '../common/OpenWithMenu'
@@ -11,7 +11,6 @@ import { getServerBaseUrl } from '../../lib/desktopRuntime'
 import { useOpenTargetStore } from '../../stores/openTargetStore'
 import { useBrowserPanelStore } from '../../stores/browserPanelStore'
 import { useWorkspacePanelStore } from '../../stores/workspacePanelStore'
-import { copyTextToClipboard } from './clipboard'
 
 type Props = {
   target: AssistantOutputTarget
@@ -53,11 +52,6 @@ export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props)
     })
   }, [sessionId, target.href])
 
-  const handleCopy = useCallback((event: ReactMouseEvent<HTMLButtonElement>) => {
-    event.stopPropagation()
-    void copyTextToClipboard(target.normalizedPath ?? target.href)
-  }, [target.href, target.normalizedPath])
-
   const handleOpenWith = useCallback((event: ReactMouseEvent<HTMLButtonElement>) => {
     event.stopPropagation()
     // Toggle: a second click on the same trigger closes the menu. OpenWithMenu's
@@ -125,15 +119,6 @@ export function AssistantOutputTargetCard({ target, sessionId, workDir }: Props)
         >
           <ExternalLink size={14} strokeWidth={2.2} aria-hidden="true" />
         </button>
-        <button
-          type="button"
-          onClick={handleCopy}
-          aria-label={t('assistantOutputs.copy')}
-          title={t('assistantOutputs.copy')}
-          className="inline-flex h-8 w-8 items-center justify-center rounded-full border border-[var(--color-border)]/70 bg-[var(--color-surface)] text-[var(--color-text-secondary)] transition-colors hover:border-[var(--color-brand)]/35 hover:text-[var(--color-text-primary)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-[var(--color-brand)]/35"
-        >
-          <Copy size={14} strokeWidth={2.2} aria-hidden="true" />
-        </button>
         <button
           type="button"
           aria-label={t('openWith.title')}
diff --git a/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx b/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
index ef3c66cc..b1b24c7a 100644
--- a/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
+++ b/desktop/src/components/chat/CurrentTurnChangeCard.test.tsx
@@ -143,6 +143,25 @@ describe('CurrentTurnChangeCard – rich file row (icon / name / type)', () => {
     expect(screen.getByText('index.ts')).toBeInTheDocument()
   })
 
+  it('sorts previewable changed files before source-only files', () => {
+    renderCard([
+      '/w/proj/package.json',
+      '/w/proj/preview.md',
+      '/w/proj/src/main.ts',
+      '/w/proj/index.html',
+      '/w/proj/style.css',
+    ])
+
+    const rows = screen.getAllByRole('button', { name: /turnChangesOpenInWorkspaceAria/ })
+    expect(rows.map((row) => row.textContent)).toEqual([
+      expect.stringContaining('preview.md'),
+      expect.stringContaining('index.html'),
+      expect.stringContaining('package.json'),
+      expect.stringContaining('main.ts'),
+      expect.stringContaining('style.css'),
+    ])
+  })
+
   it('renders the extension badge for a markdown file', () => {
     renderCard(['/w/proj/README.md'])
     // The type subtitle contains the ext in uppercase: "· MD"
diff --git a/desktop/src/components/chat/CurrentTurnChangeCard.tsx b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
index 47cddda2..c871d81e 100644
--- a/desktop/src/components/chat/CurrentTurnChangeCard.tsx
+++ b/desktop/src/components/chat/CurrentTurnChangeCard.tsx
@@ -42,10 +42,12 @@ export function CurrentTurnChangeCard({
   const [showAllFiles, setShowAllFiles] = useState(false)
 
   const files = useMemo<ChangedFileEntry[]>(
-    () => checkpoint.code.filesChanged.map((filePath) => ({
-      apiPath: filePath,
-      displayPath: relativizeWorkspacePath(filePath, workDir),
-    })),
+    () => checkpoint.code.filesChanged
+      .map((filePath) => ({
+        apiPath: filePath,
+        displayPath: relativizeWorkspacePath(filePath, workDir),
+      }))
+      .sort((a, b) => Number(isPreviewableChangedFile(b.displayPath)) - Number(isPreviewableChangedFile(a.displayPath))),
     [checkpoint.code.filesChanged, workDir],
   )
 
diff --git a/desktop/src/components/workspace/WorkspaceFileOpenWith.test.tsx b/desktop/src/components/workspace/WorkspaceFileOpenWith.test.tsx
index 057587d1..3237200f 100644
--- a/desktop/src/components/workspace/WorkspaceFileOpenWith.test.tsx
+++ b/desktop/src/components/workspace/WorkspaceFileOpenWith.test.tsx
@@ -32,20 +32,18 @@ describe('WorkspaceFileOpenWith', () => {
     vi.clearAllMocks()
   })
 
-  it('renders an item for the IDE target, the file_manager target, and a system-default item', () => {
+  it('renders only IDE and file-manager items', () => {
     const { getAllByRole } = render(
       <WorkspaceFileOpenWith absolutePath="/w/report.md" />,
     )
 
     const menuItems = getAllByRole('menuitem')
-    // IDE + file_manager + system = 3 items
-    expect(menuItems).toHaveLength(3)
+    expect(menuItems).toHaveLength(2)
 
     const labels = menuItems.map((el) => el.textContent)
     expect(labels.some((l) => l?.includes('VS Code'))).toBe(true)
     expect(labels.some((l) => l?.includes('Finder'))).toBe(true)
-    // system default item uses the 'openWith.systemDefault' key (returned as-is by mock)
-    expect(labels.some((l) => l?.includes('openWith.systemDefault'))).toBe(true)
+    expect(labels.some((l) => l?.includes('openWith.systemDefault'))).toBe(false)
   })
 
   it('clicking the IDE item calls openTarget and onAfterSelect', () => {
@@ -64,26 +62,8 @@ describe('WorkspaceFileOpenWith', () => {
     expect(onAfter).toHaveBeenCalledTimes(1)
   })
 
-  it('clicking the system-default item calls shellOpen and onAfterSelect', async () => {
-    const onAfter = vi.fn()
-    const { getAllByRole } = render(
-      <WorkspaceFileOpenWith absolutePath="/w/report.md" onAfterSelect={onAfter} />,
-    )
-
-    const menuItems = getAllByRole('menuitem')
-    const systemItem = menuItems.find((el) => el.textContent?.includes('openWith.systemDefault'))
-    if (!systemItem) throw new Error('System default menu item not found')
-
-    fireEvent.click(systemItem)
-
-    // onAfterSelect is synchronous (called before the dynamic import chain)
-    expect(onAfter).toHaveBeenCalledTimes(1)
-
-    // Flush the microtask queue for the dynamic import + .then chain
-    for (let i = 0; i < 10; i++) {
-      await Promise.resolve()
-    }
-
-    expect(shellOpen).toHaveBeenCalledWith('/w/report.md')
+  it('does not call shell open from the file open-with menu', () => {
+    render(<WorkspaceFileOpenWith absolutePath="/w/report.md" />)
+    expect(shellOpen).not.toHaveBeenCalled()
   })
 })
diff --git a/desktop/src/components/workspace/WorkspaceFileOpenWith.tsx b/desktop/src/components/workspace/WorkspaceFileOpenWith.tsx
index f3667450..40e94048 100644
--- a/desktop/src/components/workspace/WorkspaceFileOpenWith.tsx
+++ b/desktop/src/components/workspace/WorkspaceFileOpenWith.tsx
@@ -43,6 +43,8 @@ export function WorkspaceFileOpenWith({
     deps,
   )
 
+  if (items.length === 0) return null
+
   return (
     <>
       <div className="my-1 border-t border-[var(--color-border)]" role="separator" />
diff --git a/desktop/src/i18n/locales/en.ts b/desktop/src/i18n/locales/en.ts
index 86f13257..06fd47b9 100644
--- a/desktop/src/i18n/locales/en.ts
+++ b/desktop/src/i18n/locales/en.ts
@@ -96,7 +96,6 @@ export const en = {
   'openWith.title': 'Open with',
   'openWith.inAppBrowser': 'In-app browser',
   'openWith.systemBrowser': 'System browser',
-  'openWith.systemDefault': 'Open with system default',
   'openWith.workspacePreview': 'Workspace preview',
   'openWith.openInTarget': 'Open in {target}',
   'openWith.revealInTarget': 'Reveal in {target}',
@@ -113,7 +112,6 @@ export const en = {
   'assistantOutputs.kind.localhost': 'Localhost',
   'assistantOutputs.moreOutputs': '+{count} more',
   'assistantOutputs.open': 'Open',
-  'assistantOutputs.copy': 'Copy path',
 
   // ─── Workspace Panel ───────────────────────────────
   'workspace.changedFiles': 'Changed files',
diff --git a/desktop/src/i18n/locales/zh.ts b/desktop/src/i18n/locales/zh.ts
index 58216bfd..5874c2fd 100644
--- a/desktop/src/i18n/locales/zh.ts
+++ b/desktop/src/i18n/locales/zh.ts
@@ -98,7 +98,6 @@ export const zh: Record<TranslationKey, string> = {
   'openWith.title': '打开方式',
   'openWith.inAppBrowser': '应用内浏览器',
   'openWith.systemBrowser': '系统浏览器',
-  'openWith.systemDefault': '系统默认打开',
   'openWith.workspacePreview': '工作台预览',
   'openWith.openInTarget': '用 {target} 打开',
   'openWith.revealInTarget': '在 {target} 中显示',
@@ -115,7 +114,6 @@ export const zh: Record<TranslationKey, string> = {
   'assistantOutputs.kind.localhost': '本地服务',
   'assistantOutputs.moreOutputs': '+{count} 个输出',
   'assistantOutputs.open': '打开',
-  'assistantOutputs.copy': '复制路径',
 
   // ─── Workspace Panel ───────────────────────────────
   'workspace.changedFiles': '已更改文件',
diff --git a/desktop/src/lib/openWithItems.test.ts b/desktop/src/lib/openWithItems.test.ts
index f7cd6990..0811419a 100644
--- a/desktop/src/lib/openWithItems.test.ts
+++ b/desktop/src/lib/openWithItems.test.ts
@@ -114,11 +114,11 @@ describe('buildOpenWithItems – url context', () => {
 })
 
 describe('buildOpenWithItems – file context with targets', () => {
-  it('returns [preview, ide:code, fm:finder, system] ids', () => {
+  it('returns preview/open targets without a system-default fallback', () => {
     const deps = makeDeps()
     const ctx: OpenWithContext = { kind: 'file', absolutePath: '/w/a.md', relPath: 'a.md', previewable: true }
     const items = buildOpenWithItems(ctx, [ideTarget, fmTarget], deps)
-    expect(items.map((i) => i.id)).toEqual(['preview', 'ide:code', 'fm:finder', 'system'])
+    expect(items.map((i) => i.id)).toEqual(['preview', 'ide:code', 'fm:finder'])
   })
 
   it('preview calls openWorkspacePreview with relPath', () => {
@@ -139,13 +139,12 @@ describe('buildOpenWithItems – file context with targets', () => {
     expect(deps.openTarget).toHaveBeenCalledWith('code', '/w/a.md')
   })
 
-  it('system calls openSystem with absolutePath', () => {
+  it('does not include a system-default item for files', () => {
     const deps = makeDeps()
     const ctx: OpenWithContext = { kind: 'file', absolutePath: '/w/a.md', relPath: 'a.md', previewable: true }
     const items = buildOpenWithItems(ctx, [ideTarget, fmTarget], deps)
-    const sys = items.find((i) => i.id === 'system')!
-    sys.onSelect()
-    expect(deps.openSystem).toHaveBeenCalledWith('/w/a.md')
+    expect(items.some((i) => i.id === 'system')).toBe(false)
+    expect(deps.openSystem).not.toHaveBeenCalled()
   })
 
   it('ide item carries the target object', () => {
@@ -158,7 +157,7 @@ describe('buildOpenWithItems – file context with targets', () => {
 })
 
 describe('buildOpenWithItems – file context with inAppBrowserUrl (no previewable)', () => {
-  it('returns [in-app, system] ids for no targets + inAppBrowserUrl', () => {
+  it('returns only the browser preview item for no targets + inAppBrowserUrl', () => {
     const deps = makeDeps()
     const ctx: OpenWithContext = {
       kind: 'file',
@@ -166,7 +165,7 @@ describe('buildOpenWithItems – file context with inAppBrowserUrl (no previewab
       inAppBrowserUrl: 'http://127.0.0.1:4321/preview-fs/s1/page.html',
     }
     const items = buildOpenWithItems(ctx, [], deps)
-    expect(items.map((i) => i.id)).toEqual(['in-app', 'system'])
+    expect(items.map((i) => i.id)).toEqual(['in-app'])
   })
 
   it('in-app calls openInAppBrowser with inAppBrowserUrl', () => {
diff --git a/desktop/src/lib/openWithItems.ts b/desktop/src/lib/openWithItems.ts
index ecca7989..d4dc5a29 100644
--- a/desktop/src/lib/openWithItems.ts
+++ b/desktop/src/lib/openWithItems.ts
@@ -76,6 +76,5 @@ export function buildOpenWithItems(ctx: OpenWithContext, targets: OpenTarget[],
   for (const target of targets.filter((x) => x.kind === 'file_manager')) {
     items.push({ id: `fm:${target.id}`, label: deps.t('openWith.revealInTarget', { target: target.label }), icon: 'file-manager', target, onSelect: () => deps.openTarget(target.id, ctx.absolutePath) })
   }
-  items.push({ id: 'system', label: deps.t('openWith.systemDefault'), icon: 'system', onSelect: () => deps.openSystem(ctx.absolutePath) })
   return items
 }