diff --git a/src/utils/__tests__/bundledMode.test.ts b/src/utils/__tests__/bundledMode.test.ts
new file mode 100644
index 0000000000..e83901f440
--- /dev/null
+++ b/src/utils/__tests__/bundledMode.test.ts
@@ -0,0 +1,32 @@
+import { afterEach, describe, expect, test } from 'bun:test'
+import { isBunVirtualPath, isInBundledMode } from '../bundledMode.js'
+
+const originalArgv = [...process.argv]
+
+afterEach(() => {
+  process.argv = [...originalArgv]
+})
+
+describe('isBunVirtualPath', () => {
+  test('detects POSIX bun virtual filesystem paths', () => {
+    expect(isBunVirtualPath('/$bunfs/root/claude-sidecar')).toBe(true)
+  })
+
+  test('detects Windows bun virtual filesystem paths', () => {
+    expect(isBunVirtualPath('B:\\~BUN\\root\\claude-sidecar.exe')).toBe(true)
+  })
+
+  test('ignores regular filesystem paths', () => {
+    expect(isBunVirtualPath('/Applications/Claude.app/Contents/MacOS/claude-sidecar')).toBe(false)
+  })
+})
+
+describe('isInBundledMode', () => {
+  test('treats bun-compile virtual entrypoints as bundled even when embeddedFiles is empty', () => {
+    process.argv = ['bun', '/$bunfs/root/claude-sidecar']
+
+    expect(Array.isArray(Bun.embeddedFiles)).toBe(true)
+    expect(Bun.embeddedFiles.length).toBe(0)
+    expect(isInBundledMode()).toBe(true)
+  })
+})
diff --git a/src/utils/bundledMode.ts b/src/utils/bundledMode.ts
index f7e6c4dc33..3d914465b1 100644
--- a/src/utils/bundledMode.ts
+++ b/src/utils/bundledMode.ts
@@ -9,14 +9,31 @@ export function isRunningWithBun(): boolean {
   return process.versions.bun !== undefined
 }
 
+const BUN_VIRTUAL_PATH_MARKERS = ['/$bunfs/', '/~bun/']
+
+export function isBunVirtualPath(candidatePath: string | null | undefined): boolean {
+  if (!candidatePath) {
+    return false
+  }
+
+  const normalized = candidatePath.replace(/\\/g, '/').toLowerCase()
+  return BUN_VIRTUAL_PATH_MARKERS.some(marker => normalized.includes(marker))
+}
+
 /**
  * Detects if running as a Bun-compiled standalone executable.
- * This checks for embedded files which are present in compiled binaries.
+ * Bun compile loads the entry module from Bun's virtual filesystem
+ * (`/$bunfs/...` on POSIX, `~BUN\\...` on Windows). `Bun.embeddedFiles`
+ * alone is not sufficient because compiled binaries can still report an
+ * empty embedded file list at runtime.
  */
 export function isInBundledMode(): boolean {
+  if (typeof Bun === 'undefined') {
+    return false
+  }
+
   return (
-    typeof Bun !== 'undefined' &&
-    Array.isArray(Bun.embeddedFiles) &&
-    Bun.embeddedFiles.length > 0
+    isBunVirtualPath(process.argv[1]) ||
+    (Array.isArray(Bun.embeddedFiles) && Bun.embeddedFiles.length > 0)
   )
 }
diff --git a/src/utils/ripgrep.ts b/src/utils/ripgrep.ts
index 8128aae779..37e0d398be 100644
--- a/src/utils/ripgrep.ts
+++ b/src/utils/ripgrep.ts
@@ -6,7 +6,7 @@ import { homedir } from 'os'
 import * as path from 'path'
 import { logEvent } from 'src/services/analytics/index.js'
 import { fileURLToPath } from 'url'
-import { isInBundledMode } from './bundledMode.js'
+import { isBunVirtualPath, isInBundledMode } from './bundledMode.js'
 import { logForDebugging } from './debug.js'
 import { isEnvDefinedFalsy } from './envUtils.js'
 import { execFileNoThrow } from './execFileNoThrow.js'
@@ -22,8 +22,6 @@ const __dirname = path.join(
   process.env.NODE_ENV === 'test' ? '../../../' : '../',
 )
 
-const BUN_VIRTUAL_PATH_MARKERS = ['$bunfs', '~BUN']
-
 type RipgrepConfig = {
   mode: 'system' | 'builtin' | 'embedded' | 'unavailable'
   command: string
@@ -31,11 +29,6 @@ type RipgrepConfig = {
   argv0?: string
 }
 
-function isBunVirtualPath(candidatePath: string): boolean {
-  const normalized = candidatePath.replace(/\\/g, '/')
-  return BUN_VIRTUAL_PATH_MARKERS.some(marker => normalized.includes(marker))
-}
-
 export function isUsableBuiltinRipgrepPath(candidatePath: string): boolean {
   return !isBunVirtualPath(candidatePath) && existsSync(candidatePath)
 }