diff --git a/packages/cli/src/serve/run-qwen-serve.test.ts b/packages/cli/src/serve/run-qwen-serve.test.ts
index 9a40063fda1..906891dea3f 100644
--- a/packages/cli/src/serve/run-qwen-serve.test.ts
+++ b/packages/cli/src/serve/run-qwen-serve.test.ts
@@ -34,6 +34,7 @@ import {
   waitForRuntimeStartingForShutdown,
 } from './run-qwen-serve.js';
 import { isBrowserAutomationMcpAvailable } from './cdp-mcp-command.js';
+import * as nativeDirectoryPicker from './native-directory-picker.js';
 import { loadServeFastPathEnvironment } from './fast-path-settings.js';
 import { loadEnvironment } from '../config/environment.js';
 import { RUNTIME_STARTUP_CANCELLED_MESSAGE } from './runtime-startup-errors.js';
@@ -10615,6 +10616,61 @@ describe('runQwenServe runtime startup failures', () => {
     }
   });
 
+  it.each([true, false])(
+    'mirrors the native directory picker probe on the bootstrap envelopes (available: %s)',
+    async (available) => {
+      tmpDir = fs.realpathSync(
+        fs.mkdtempSync(path.join(os.tmpdir(), 'qws-bootstrap-picker-')),
+      );
+      // Keep the runtime from mounting so the bootstrap `/capabilities` and
+      // `/daemon/status` envelopes stay the ones being served.
+      vi.spyOn(acpBridge, 'createAcpSessionBridge').mockImplementation(() => {
+        throw new Error('runtime boom');
+      });
+      const probe = vi
+        .spyOn(nativeDirectoryPicker, 'isNativeDirectoryPickerAvailable')
+        .mockReturnValue(available);
+      const handle = await runQwenServe(
+        {
+          port: 0,
+          hostname: '127.0.0.1',
+          mode: 'http-bridge',
+          workspace: tmpDir,
+          maxSessions: 1,
+          serveWebShell: false,
+        },
+        { resolveOnListen: true },
+      );
+      try {
+        await expect(handle.runtimeReady).rejects.toThrow('runtime boom');
+        const probeCallsAfterBoot = probe.mock.calls.length;
+        const capabilities = (await (
+          await fetch(`${handle.url}/capabilities`)
+        ).json()) as { features: string[] };
+        const status = (await (
+          await fetch(`${handle.url}/daemon/status`)
+        ).json()) as { capabilities: { features: string[] } };
+        if (available) {
+          expect(capabilities.features).toContain('native_directory_picker');
+          expect(status.capabilities.features).toContain(
+            'native_directory_picker',
+          );
+        } else {
+          expect(capabilities.features).not.toContain(
+            'native_directory_picker',
+          );
+          expect(status.capabilities.features).not.toContain(
+            'native_directory_picker',
+          );
+        }
+        // Probed once while the bootstrap app was built, not per request.
+        expect(probe.mock.calls.length).toBe(probeCallsAfterBoot);
+      } finally {
+        await handle.close();
+      }
+    },
+  );
+
   it('shuts down a bridge when runtime mounting fails after bridge creation', async () => {
     tmpDir = fs.realpathSync(
       fs.mkdtempSync(path.join(os.tmpdir(), 'qws-runtime-partial-fail-')),
diff --git a/packages/cli/src/serve/run-qwen-serve.ts b/packages/cli/src/serve/run-qwen-serve.ts
index f84fb6021fc..ac96b3d5257 100644
--- a/packages/cli/src/serve/run-qwen-serve.ts
+++ b/packages/cli/src/serve/run-qwen-serve.ts
@@ -112,6 +112,7 @@ import {
   getServeProtocolVersions,
   SERVE_CAPABILITY_REGISTRY,
 } from './capabilities.js';
+import { isNativeDirectoryPickerAvailable } from './native-directory-picker.js';
 import {
   EXTERNAL_TOOL_GUARD_PROVIDER_ATTACHED_VALUE,
   EXTERNAL_TOOL_GUARD_REQUIRED_VALUE,
@@ -2289,6 +2290,7 @@ function currentServeFeaturesForRunQwenServe(
   sessionArtifactsPersistenceAvailable: boolean,
   currentSessionSchedulingAvailable: boolean,
   env: Readonly<Record<string, string | undefined>>,
+  nativeDirectoryPickerAvailable: boolean,
 ): string[] {
   return getAdvertisedServeFeatures(undefined, {
     requireAuth: opts.requireAuth === true,
@@ -2315,8 +2317,10 @@ function currentServeFeaturesForRunQwenServe(
     channelManagementAvailable: true,
     persistentWorkspaceRegistrationAvailable: true,
     workspaceRuntimeRemovalAvailable: true,
-    // Advertise the same WS feature flags as the runtime path (serve-features.ts)
-    // so the bootstrap `/capabilities` window doesn't briefly under-report them.
+    // Advertise the same host-conditional and WS feature flags as the runtime
+    // path (serve-features.ts) so the bootstrap `/capabilities` window doesn't
+    // briefly under-report them.
+    nativeDirectoryPickerAvailable,
     clientMcpOverWsEnabled: opts.clientMcpOverWs === true,
     cdpTunnelOverWsEnabled: opts.cdpTunnelOverWs === true,
     browserAutomationMcpAvailable: isBrowserAutomationMcpAvailable(opts, env),
@@ -2332,6 +2336,7 @@ function createBootstrapCapabilities(input: {
   currentSessionSchedulingAvailable: boolean;
   permissionPolicy: PermissionPolicy | undefined;
   env: Readonly<Record<string, string | undefined>>;
+  nativeDirectoryPickerAvailable: boolean;
 }): CapabilitiesEnvelope {
   return {
     v: CAPABILITIES_SCHEMA_VERSION,
@@ -2346,6 +2351,7 @@ function createBootstrapCapabilities(input: {
       input.sessionArtifactsPersistenceAvailable,
       input.currentSessionSchedulingAvailable,
       input.env,
+      input.nativeDirectoryPickerAvailable,
     ),
     modelServices: [],
     workspaceCwd: input.boundWorkspace,
@@ -2566,6 +2572,11 @@ function createBootstrapServeApp(input: {
     onHealthServed,
   } = input;
   const app = express();
+  // The probe stats `/dev/console` (macOS) or scans `PATH` for `zenity`
+  // (Linux), and both bootstrap endpoints below rebuild their envelope per
+  // request, so evaluate it once here — the runtime path likewise probes once,
+  // at `createApp` time (server.ts).
+  const nativeDirectoryPickerAvailable = isNativeDirectoryPickerAvailable();
 
   installSameOriginOriginStrip(app, getPort);
   if (opts.allowOrigins && opts.allowOrigins.length > 0) {
@@ -2626,6 +2637,7 @@ function createBootstrapServeApp(input: {
         currentSessionSchedulingAvailable,
         permissionPolicy,
         env: process.env,
+        nativeDirectoryPickerAvailable,
       }),
     );
   });
@@ -2765,6 +2777,7 @@ function createBootstrapServeApp(input: {
           sessionArtifactsPersistenceAvailable,
           currentSessionSchedulingAvailable,
           process.env,
+          nativeDirectoryPickerAvailable,
         ),
       },
       runtime: {