diff --git a/desktop/src/components/chat/ChatInput.test.tsx b/desktop/src/components/chat/ChatInput.test.tsx
index 80185257..cd9953e2 100644
--- a/desktop/src/components/chat/ChatInput.test.tsx
+++ b/desktop/src/components/chat/ChatInput.test.tsx
@@ -520,7 +520,7 @@ describe('ChatInput file mentions', () => {
       },
     })
 
-    fireEvent.click(await screen.findByText('conditions.py'))
+    fireEvent.click(await screen.findByText('backend/src/conditions.py'))
 
     await waitFor(() => {
       expect(input.value).toBe('记一下这个文件讲了什么东西。')
diff --git a/desktop/src/components/chat/FileSearchMenu.test.tsx b/desktop/src/components/chat/FileSearchMenu.test.tsx
index b5a70cef..e44f4569 100644
--- a/desktop/src/components/chat/FileSearchMenu.test.tsx
+++ b/desktop/src/components/chat/FileSearchMenu.test.tsx
@@ -91,7 +91,7 @@ describe('FileSearchMenu', () => {
       />,
     )
 
-    fireEvent.click(await screen.findByText('backend'))
+    fireEvent.click(await screen.findByText('backend/'))
 
     expect(onSelect).toHaveBeenCalledWith('/repo/backend', 'backend', true)
     expect(onNavigate).not.toHaveBeenCalled()
@@ -132,11 +132,36 @@ describe('FileSearchMenu', () => {
       />,
     )
 
-    fireEvent.click(await screen.findByText('pictactic'))
+    fireEvent.click(await screen.findByText('backend/src/pictactic'))
 
     expect(onSelect).toHaveBeenCalledWith('/repo/backend/src/pictactic', 'backend/src/pictactic', false)
   })
 
+  it('renders search results as insertable paths instead of repeated basenames', async () => {
+    vi.mocked(filesystemApi.search).mockResolvedValueOnce({
+      currentPath: '/repo',
+      parentPath: '/',
+      query: 'src',
+      entries: [
+        { name: 'src', path: '/repo/src', relativePath: 'src', isDirectory: true },
+        { name: 'hooks', path: '/repo/src/hooks', relativePath: 'src/hooks', isDirectory: true },
+        { name: 'src', path: '/repo/desktop/src', relativePath: 'desktop/src', isDirectory: true },
+      ],
+    })
+
+    render(
+      <FileSearchMenu
+        cwd="/repo"
+        filter="src"
+        onSelect={() => {}}
+      />,
+    )
+
+    expect(await screen.findByText('src/')).toBeInTheDocument()
+    expect(screen.getByText('src/hooks/')).toBeInTheDocument()
+    expect(screen.getByText('desktop/src/')).toBeInTheDocument()
+  })
+
   it('uses the resolved home root for typed folder filters when no workspace is selected', async () => {
     vi.mocked(filesystemApi.search).mockResolvedValueOnce({
       currentPath: '/Users/nanmi',
@@ -160,7 +185,7 @@ describe('FileSearchMenu', () => {
       />,
     )
 
-    expect(await screen.findByText('workspace')).toBeInTheDocument()
+    expect(await screen.findByText('workspace/')).toBeInTheDocument()
 
     rerender(
       <FileSearchMenu
diff --git a/desktop/src/components/chat/FileSearchMenu.tsx b/desktop/src/components/chat/FileSearchMenu.tsx
index 7b065f3b..47dacf65 100644
--- a/desktop/src/components/chat/FileSearchMenu.tsx
+++ b/desktop/src/components/chat/FileSearchMenu.tsx
@@ -68,6 +68,12 @@ export const FileSearchMenu = forwardRef<FileSearchMenuHandle, Props>(({ cwd, fi
     return entry.name
   }, [cwd, rootPath])
 
+  const getDisplayPath = useCallback((entry: DirEntry) => {
+    const relativePath = getRelativePath(entry).replace(/\\/g, '/')
+    if (!entry.isDirectory) return relativePath
+    return `${relativePath.replace(/\/+$/, '')}/`
+  }, [getRelativePath])
+
   const selectEntry = useCallback((entry: DirEntry) => {
     onSelect(entry.path, getRelativePath(entry), entry.isDirectory)
   }, [getRelativePath, onSelect])
@@ -194,6 +200,7 @@ export const FileSearchMenu = forwardRef<FileSearchMenuHandle, Props>(({ cwd, fi
 
   const renderEntry = (entry: DirEntry, index: number) => {
     const relativePath = getRelativePath(entry)
+    const displayPath = getDisplayPath(entry)
     const parentPath = relativePath.split('/').slice(0, -1).join('/')
     const selected = selectedIndex === index
     return (
@@ -208,7 +215,9 @@ export const FileSearchMenu = forwardRef<FileSearchMenuHandle, Props>(({ cwd, fi
         <button
           type="button"
           onClick={() => selectEntry(entry)}
-          className="flex min-w-0 flex-1 items-center gap-3 rounded-lg px-2.5 py-2 text-left transition-colors hover:bg-[var(--color-surface-hover)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-[var(--color-brand)]/40"
+          className={`flex min-w-0 flex-1 items-center rounded-lg px-2.5 text-left transition-colors hover:bg-[var(--color-surface-hover)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-[var(--color-brand)]/40 ${
+            isSearchMode ? 'gap-2.5 py-2' : 'gap-3 py-2'
+          }`}
           role="option"
           aria-selected={selected}
         >
@@ -216,14 +225,27 @@ export const FileSearchMenu = forwardRef<FileSearchMenuHandle, Props>(({ cwd, fi
             {entry.isDirectory ? 'folder' : 'description'}
           </span>
           <span className="min-w-0 flex-1">
-            <span className="block truncate text-sm font-medium text-[var(--color-text-primary)]">{entry.name}</span>
-            <span className="block truncate font-[var(--font-mono)] text-[11px] text-[var(--color-text-tertiary)]">
-              {parentPath || (entry.isDirectory ? t('fileSearch.directory') : t('fileSearch.currentDirectory'))}
+            {isSearchMode ? (
+              <span
+                className="block truncate font-[var(--font-mono)] text-sm text-[var(--color-text-primary)]"
+                title={displayPath}
+              >
+                {displayPath}
+              </span>
+            ) : (
+              <>
+                <span className="block truncate text-sm font-medium text-[var(--color-text-primary)]">{entry.name}</span>
+                <span className="block truncate font-[var(--font-mono)] text-[11px] text-[var(--color-text-tertiary)]">
+                  {parentPath || (entry.isDirectory ? t('fileSearch.directory') : t('fileSearch.currentDirectory'))}
+                </span>
+              </>
+            )}
+          </span>
+          {!isSearchMode ? (
+            <span className="shrink-0 rounded-md border border-[var(--color-border)] px-1.5 py-0.5 text-[10px] font-medium uppercase tracking-[0.02em] text-[var(--color-text-tertiary)]">
+              {entry.isDirectory ? t('fileSearch.folderTag') : t('fileSearch.fileTag')}
             </span>
-          </span>
-          <span className="shrink-0 rounded-md border border-[var(--color-border)] px-1.5 py-0.5 text-[10px] font-medium uppercase tracking-[0.02em] text-[var(--color-text-tertiary)]">
-            {entry.isDirectory ? t('fileSearch.folderTag') : t('fileSearch.fileTag')}
-          </span>
+          ) : null}
         </button>
         {entry.isDirectory ? (
           <button
diff --git a/src/server/__tests__/filesystem.test.ts b/src/server/__tests__/filesystem.test.ts
index 02ccaf98..0e2ffdc2 100644
--- a/src/server/__tests__/filesystem.test.ts
+++ b/src/server/__tests__/filesystem.test.ts
@@ -56,6 +56,9 @@ describe('filesystem API', () => {
     await fsp.mkdir(path.join(homeFixtureDir, 'src', 'commands'), { recursive: true })
     await fsp.mkdir(path.join(homeFixtureDir, 'src', 'commands', 'files'), { recursive: true })
     await fsp.mkdir(path.join(homeFixtureDir, 'src', 'constants'), { recursive: true })
+    await fsp.mkdir(path.join(homeFixtureDir, 'src', 'hooks'), { recursive: true })
+    await fsp.mkdir(path.join(homeFixtureDir, 'desktop', 'src'), { recursive: true })
+    await fsp.mkdir(path.join(homeFixtureDir, 'scripts', 'quality-gate', 'baseline', 'fixtures', 'cross-module-refactor', 'src'), { recursive: true })
     await fsp.mkdir(path.join(homeFixtureDir, '__pycache__'), { recursive: true })
     await fsp.mkdir(path.join(homeFixtureDir, 'node_modules', 'pkg'), { recursive: true })
     await fsp.mkdir(path.join(homeFixtureDir, '.venv', 'lib'), { recursive: true })
@@ -65,6 +68,9 @@ describe('filesystem API', () => {
     await fsp.writeFile(path.join(homeFixtureDir, 'src', 'commands', 'files.ts'), 'export {}')
     await fsp.writeFile(path.join(homeFixtureDir, 'src', 'commands', 'files', 'index.ts'), 'export {}')
     await fsp.writeFile(path.join(homeFixtureDir, 'src', 'constants', 'fileSearch.ts'), 'export {}')
+    await fsp.writeFile(path.join(homeFixtureDir, 'src', 'hooks', 'useFileSearch.ts'), 'export {}')
+    await fsp.writeFile(path.join(homeFixtureDir, 'desktop', 'src', 'main.ts'), 'export {}')
+    await fsp.writeFile(path.join(homeFixtureDir, 'scripts', 'quality-gate', 'baseline', 'fixtures', 'cross-module-refactor', 'src', 'index.ts'), 'export {}')
     await fsp.writeFile(path.join(homeFixtureDir, '__pycache__', 'fileSearch.cpython-311.pyc'), '')
     await fsp.writeFile(path.join(homeFixtureDir, 'node_modules', 'pkg', 'files.js'), '')
     await fsp.writeFile(path.join(homeFixtureDir, '.venv', 'lib', 'files.py'), '')
@@ -94,6 +100,25 @@ describe('filesystem API', () => {
     expect(body.entries.some((entry) => entry.relativePath === 'node_modules/pkg/files.js')).toBe(false)
     expect(body.entries.some((entry) => entry.relativePath === '.venv/lib/files.py')).toBe(false)
     expect(body.entries.some((entry) => entry.relativePath === 'tmp-ignore/files.tmp')).toBe(false)
+
+    const srcRes = await handleFilesystemRoute(
+      '/api/filesystem/browse',
+      makeUrl('/api/filesystem/browse', {
+        path: homeFixtureDir,
+        search: 'src',
+        includeFiles: 'true',
+      }),
+    )
+
+    expect(srcRes.status).toBe(200)
+    const srcBody = await srcRes.json() as { entries: Array<{ relativePath?: string }> }
+    const srcPaths = srcBody.entries.map(entry => entry.relativePath)
+    expect(srcPaths[0]).toBe('src')
+    expect(srcPaths.indexOf('src/hooks')).toBeGreaterThan(-1)
+    expect(srcPaths.indexOf('desktop/src')).toBeGreaterThan(-1)
+    expect(srcPaths.indexOf('scripts/quality-gate/baseline/fixtures/cross-module-refactor/src')).toBeGreaterThan(-1)
+    expect(srcPaths.indexOf('src/hooks')).toBeLessThan(srcPaths.indexOf('desktop/src'))
+    expect(srcPaths.indexOf('src/hooks')).toBeLessThan(srcPaths.indexOf('scripts/quality-gate/baseline/fixtures/cross-module-refactor/src'))
   })
 
   it('falls back to ripgrep search outside git and still respects ignore files', async () => {
diff --git a/src/server/api/filesystem.ts b/src/server/api/filesystem.ts
index a691cdb8..97f68676 100644
--- a/src/server/api/filesystem.ts
+++ b/src/server/api/filesystem.ts
@@ -204,6 +204,11 @@ async function searchFilesystemEntries(
     .sort((a, b) => {
       if (a.score !== b.score) return b.score - a.score
       if (a.isDirectory !== b.isDirectory) return a.isDirectory ? -1 : 1
+      const aPath = a.relativePath ?? a.name
+      const bPath = b.relativePath ?? b.name
+      const aDepth = pathDepth(aPath)
+      const bDepth = pathDepth(bPath)
+      if (aDepth !== bDepth) return aDepth - bDepth
       return (a.relativePath ?? a.name).localeCompare(b.relativePath ?? b.name)
     })
     .slice(0, options.maxResults)
@@ -386,13 +391,16 @@ function scoreFilesystemEntry(name: string, relativePath: string, query: string,
   const normalizedName = normalizeSearchText(name)
   const normalizedPath = normalizeSearchText(relativePath)
   const pathNoExtension = normalizedPath.replace(/\.[^/.]+$/, '')
+  const pathPrefix = `${query}/`
   const baseBoost = isDirectory ? 4 : 0
   const depthPenalty = Math.min(relativePath.split('/').length - 1, 8) * 2
 
-  if (normalizedName === query) return 120 + baseBoost - depthPenalty
-  if (pathNoExtension === query || normalizedPath === query) return 112 + baseBoost - depthPenalty
-  if (normalizedName.startsWith(query)) return 96 + baseBoost - depthPenalty
-  if (normalizedPath.startsWith(query)) return 88 + baseBoost - depthPenalty
+  if (normalizedPath === query) return 150 + baseBoost - depthPenalty
+  if (pathNoExtension === query) return 144 + baseBoost - depthPenalty
+  if (normalizedPath.startsWith(pathPrefix)) return 136 + baseBoost - depthPenalty
+  if (normalizedPath.startsWith(query)) return 112 + baseBoost - depthPenalty
+  if (normalizedName === query) return 96 + baseBoost - depthPenalty
+  if (normalizedName.startsWith(query)) return 88 + baseBoost - depthPenalty
   if (normalizedName.includes(query)) return 72 + baseBoost - depthPenalty
   if (normalizedPath.includes(query)) return 60 + baseBoost - depthPenalty
 
@@ -405,6 +413,10 @@ function scoreFilesystemEntry(name: string, relativePath: string, query: string,
   return 0
 }
 
+function pathDepth(relativePath: string): number {
+  return relativePath.split('/').length
+}
+
 function fuzzyScore(value: string, query: string): number {
   let queryIndex = 0
   let runLength = 0