Add support for sensitive keychain-stored per-extension settings (#11953)

packages/cli/src/commands/extensions/disable.ts

@@ -17,7 +17,7 @@ interface DisableArgs {
   scope?: string;
 }
 
-export function handleDisable(args: DisableArgs) {
+export async function handleDisable(args: DisableArgs) {
   const workspaceDir = process.cwd();
   const extensionManager = new ExtensionManager({
     workspaceDir,
@@ -25,13 +25,16 @@ export function handleDisable(args: DisableArgs) {
     requestSetting: promptForSetting,
     settings: loadSettings(workspaceDir).merged,
   });
-  extensionManager.loadExtensions();
+  await extensionManager.loadExtensions();
 
   try {
     if (args.scope?.toLowerCase() === 'workspace') {
-      extensionManager.disableExtension(args.name, SettingScope.Workspace);
+      await extensionManager.disableExtension(
+        args.name,
+        SettingScope.Workspace,
+      );
     } else {
-      extensionManager.disableExtension(args.name, SettingScope.User);
+      await extensionManager.disableExtension(args.name, SettingScope.User);
     }
     debugLogger.log(
       `Extension "${args.name}" successfully disabled for scope "${args.scope}".`,

packages/cli/src/commands/extensions/enable.ts

@@ -20,7 +20,7 @@ interface EnableArgs {
   scope?: string;
 }
 
-export function handleEnable(args: EnableArgs) {
+export async function handleEnable(args: EnableArgs) {
   const workingDir = process.cwd();
   const extensionManager = new ExtensionManager({
     workspaceDir: workingDir,
@@ -28,7 +28,7 @@ export function handleEnable(args: EnableArgs) {
     requestSetting: promptForSetting,
     settings: loadSettings(workingDir).merged,
   });
-  extensionManager.loadExtensions();
+  await extensionManager.loadExtensions();
 
   try {
     if (args.scope?.toLowerCase() === 'workspace') {

packages/cli/src/commands/extensions/install.ts

@@ -76,7 +76,7 @@ export async function handleInstall(args: InstallArgs) {
       requestSetting: promptForSetting,
       settings: loadSettings(workspaceDir).merged,
     });
-    extensionManager.loadExtensions();
+    await extensionManager.loadExtensions();
     const name =
       await extensionManager.installOrUpdateExtension(installMetadata);
     debugLogger.log(`Extension "${name}" installed successfully and enabled.`);

packages/cli/src/commands/extensions/link.ts

@@ -33,7 +33,7 @@ export async function handleLink(args: InstallArgs) {
       requestSetting: promptForSetting,
       settings: loadSettings(workspaceDir).merged,
     });
-    extensionManager.loadExtensions();
+    await extensionManager.loadExtensions();
     const extensionName =
       await extensionManager.installOrUpdateExtension(installMetadata);
     debugLogger.log(

packages/cli/src/commands/extensions/list.ts

@@ -21,7 +21,7 @@ export async function handleList() {
       requestSetting: promptForSetting,
       settings: loadSettings(workspaceDir).merged,
     });
-    const extensions = extensionManager.loadExtensions();
+    const extensions = await extensionManager.loadExtensions();
     if (extensions.length === 0) {
       debugLogger.log('No extensions installed.');
       return;

packages/cli/src/commands/extensions/uninstall.ts

@@ -25,7 +25,7 @@ export async function handleUninstall(args: UninstallArgs) {
       requestSetting: promptForSetting,
       settings: loadSettings(workspaceDir).merged,
     });
-    extensionManager.loadExtensions();
+    await extensionManager.loadExtensions();
     await extensionManager.uninstallExtension(args.name, false);
     debugLogger.log(`Extension "${args.name}" successfully uninstalled.`);
   } catch (error) {

packages/cli/src/commands/extensions/update.ts

@@ -37,7 +37,7 @@ export async function handleUpdate(args: UpdateArgs) {
     settings: loadSettings(workspaceDir).merged,
   });
 
-  const extensions = extensionManager.loadExtensions();
+  const extensions = await extensionManager.loadExtensions();
   if (args.name) {
     try {
       const extension = extensions.find(

packages/cli/src/commands/mcp/list.ts

@@ -33,7 +33,7 @@ async function getMcpServersFromConfig(): Promise<
     requestConsent: requestConsentNonInteractive,
     requestSetting: promptForSetting,
   });
-  const extensions = extensionManager.loadExtensions();
+  const extensions = await extensionManager.loadExtensions();
   const mcpServers = { ...(settings.merged.mcpServers || {}) };
   for (const extension of extensions) {
     Object.entries(extension.mcpServers || {}).forEach(([key, server]) => {

packages/cli/src/config/config.ts

@@ -423,7 +423,7 @@ export async function loadCliConfig(
     workspaceDir: cwd,
     enabledExtensionOverrides: argv.extensions,
   });
-  extensionManager.loadExtensions();
+  await extensionManager.loadExtensions();
 
   // Call the (now wrapper) loadHierarchicalGeminiMemory which calls the server's version
   const { memoryContent, fileCount, filePaths } =

packages/cli/src/config/extension-manager.ts

@@ -133,7 +133,7 @@ export class ExtensionManager implements ExtensionLoader {
     const isUpdate = !!previousExtensionConfig;
     let newExtensionConfig: ExtensionConfig | null = null;
     let localSourcePath: string | undefined;
-    let extension: GeminiCLIExtension;
+    let extension: GeminiCLIExtension | null;
     try {
       if (!isWorkspaceTrusted(this.settings).isTrusted) {
         throw new Error(
@@ -243,12 +243,16 @@ export class ExtensionManager implements ExtensionLoader {
           this.requestConsent,
           previousExtensionConfig,
         );
-
-        const extensionStorage = new ExtensionStorage(newExtensionName);
-        const destinationPath = extensionStorage.getExtensionDir();
+        const extensionId = getExtensionId(newExtensionConfig, installMetadata);
+        const destinationPath = new ExtensionStorage(
+          newExtensionName,
+        ).getExtensionDir();
         let previousSettings: Record<string, string> | undefined;
         if (isUpdate) {
-          previousSettings = getEnvContents(extensionStorage);
+          previousSettings = await getEnvContents(
+            previousExtensionConfig,
+            extensionId,
+          );
           await this.uninstallExtension(newExtensionName, isUpdate);
         }
 
@@ -257,6 +261,7 @@ export class ExtensionManager implements ExtensionLoader {
           if (isUpdate) {
             await maybePromptForSettings(
               newExtensionConfig,
+              extensionId,
               this.requestSetting,
               previousExtensionConfig,
               previousSettings,
@@ -264,6 +269,7 @@ export class ExtensionManager implements ExtensionLoader {
           } else {
             await maybePromptForSettings(
               newExtensionConfig,
+              extensionId,
               this.requestSetting,
             );
           }
@@ -286,7 +292,10 @@ export class ExtensionManager implements ExtensionLoader {
 
         // TODO: Gracefully handle this call failing, we should back up the old
         // extension prior to overwriting it and then restore it.
-        extension = this.loadExtension(destinationPath)!;
+        extension = await this.loadExtension(destinationPath)!;
+        if (!extension) {
+          throw new Error(`Extension not found`);
+        }
         if (isUpdate) {
           logExtensionUpdateEvent(
             this.telemetryConfig,
@@ -401,7 +410,7 @@ export class ExtensionManager implements ExtensionLoader {
     this.eventEmitter.emit('extensionUninstalled', { extension });
   }
 
-  loadExtensions(): GeminiCLIExtension[] {
+  async loadExtensions(): Promise<GeminiCLIExtension[]> {
     if (this.loadedExtensions) {
       throw new Error('Extensions already loaded, only load extensions once.');
     }
@@ -413,12 +422,14 @@ export class ExtensionManager implements ExtensionLoader {
     for (const subdir of fs.readdirSync(extensionsDir)) {
       const extensionDir = path.join(extensionsDir, subdir);
 
-      this.loadExtension(extensionDir);
+      await this.loadExtension(extensionDir);
     }
     return this.loadedExtensions;
   }
 
-  private loadExtension(extensionDir: string): GeminiCLIExtension | null {
+  private async loadExtension(
+    extensionDir: string,
+  ): Promise<GeminiCLIExtension | null> {
     this.loadedExtensions ??= [];
     if (!fs.statSync(extensionDir).isDirectory()) {
       return null;
@@ -441,7 +452,10 @@ export class ExtensionManager implements ExtensionLoader {
         );
       }
 
-      const customEnv = getEnvContents(new ExtensionStorage(config.name));
+      const customEnv = await getEnvContents(
+        config,
+        getExtensionId(config, installMetadata),
+      );
       config = resolveEnvVarsInObject(config, customEnv);
 
       if (config.mcpServers) {
@@ -573,7 +587,7 @@ export class ExtensionManager implements ExtensionLoader {
     return output;
   }
 
-  disableExtension(name: string, scope: SettingScope) {
+  async disableExtension(name: string, scope: SettingScope) {
     if (
       scope === SettingScope.System ||
       scope === SettingScope.SystemDefaults
@@ -598,7 +612,7 @@ export class ExtensionManager implements ExtensionLoader {
     this.eventEmitter.emit('extensionDisabled', { extension });
   }
 
-  enableExtension(name: string, scope: SettingScope) {
+  async enableExtension(name: string, scope: SettingScope) {
     if (
       scope === SettingScope.System ||
       scope === SettingScope.SystemDefaults

packages/cli/src/config/extension.test.ts

@@ -13,6 +13,7 @@ import {
   ExtensionUninstallEvent,
   ExtensionDisableEvent,
   ExtensionEnableEvent,
+  KeychainTokenStorage,
 } from '@google/gemini-cli-core';
 import { loadSettings, SettingScope } from './settings.js';
 import { isWorkspaceTrusted } from './trustedFolders.js';
@@ -96,6 +97,13 @@ vi.mock('@google/gemini-cli-core', async (importOriginal) => {
     ExtensionInstallEvent: vi.fn(),
     ExtensionUninstallEvent: vi.fn(),
     ExtensionDisableEvent: vi.fn(),
+    KeychainTokenStorage: vi.fn().mockImplementation(() => ({
+      getSecret: vi.fn(),
+      setSecret: vi.fn(),
+      deleteSecret: vi.fn(),
+      listSecrets: vi.fn(),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    })),
   };
 });
 
@@ -107,6 +115,14 @@ vi.mock('child_process', async (importOriginal) => {
   };
 });
 
+interface MockKeychainStorage {
+  getSecret: ReturnType<typeof vi.fn>;
+  setSecret: ReturnType<typeof vi.fn>;
+  deleteSecret: ReturnType<typeof vi.fn>;
+  listSecrets: ReturnType<typeof vi.fn>;
+  isAvailable: ReturnType<typeof vi.fn>;
+}
+
 describe('extension tests', () => {
   let tempHomeDir: string;
   let tempWorkspaceDir: string;
@@ -116,8 +132,32 @@ describe('extension tests', () => {
   let mockPromptForSettings: MockedFunction<
     (setting: ExtensionSetting) => Promise<string>
   >;
+  let mockKeychainStorage: MockKeychainStorage;
+  let keychainData: Record<string, string>;
 
   beforeEach(() => {
+    vi.clearAllMocks();
+    keychainData = {};
+    mockKeychainStorage = {
+      getSecret: vi
+        .fn()
+        .mockImplementation(async (key: string) => keychainData[key] || null),
+      setSecret: vi
+        .fn()
+        .mockImplementation(async (key: string, value: string) => {
+          keychainData[key] = value;
+        }),
+      deleteSecret: vi.fn().mockImplementation(async (key: string) => {
+        delete keychainData[key];
+      }),
+      listSecrets: vi
+        .fn()
+        .mockImplementation(async () => Object.keys(keychainData)),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    };
+    (
+      KeychainTokenStorage as unknown as ReturnType<typeof vi.fn>
+    ).mockImplementation(() => mockKeychainStorage);
     tempHomeDir = fs.mkdtempSync(
       path.join(os.tmpdir(), 'gemini-cli-test-home-'),
     );
@@ -151,7 +191,7 @@ describe('extension tests', () => {
   });
 
   describe('loadExtensions', () => {
-    it('should include extension path in loaded extension', () => {
+    it('should include extension path in loaded extension', async () => {
       const extensionDir = path.join(userExtensionsDir, 'test-extension');
       fs.mkdirSync(extensionDir, { recursive: true });
 
@@ -161,13 +201,13 @@ describe('extension tests', () => {
         version: '1.0.0',
       });
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
       expect(extensions).toHaveLength(1);
       expect(extensions[0].path).toBe(extensionDir);
       expect(extensions[0].name).toBe('test-extension');
     });
 
-    it('should load context file path when GEMINI.md is present', () => {
+    it('should load context file path when GEMINI.md is present', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
@@ -180,7 +220,7 @@ describe('extension tests', () => {
         version: '2.0.0',
       });
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(2);
       const ext1 = extensions.find((e) => e.name === 'ext1');
@@ -191,7 +231,7 @@ describe('extension tests', () => {
       expect(ext2?.contextFiles).toEqual([]);
     });
 
-    it('should load context file path from the extension config', () => {
+    it('should load context file path from the extension config', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
@@ -200,7 +240,7 @@ describe('extension tests', () => {
         contextFileName: 'my-context-file.md',
       });
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(1);
       const ext1 = extensions.find((e) => e.name === 'ext1');
@@ -209,7 +249,7 @@ describe('extension tests', () => {
       ]);
     });
 
-    it('should annotate disabled extensions', () => {
+    it('should annotate disabled extensions', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'disabled-extension',
@@ -220,8 +260,8 @@ describe('extension tests', () => {
         name: 'enabled-extension',
         version: '2.0.0',
       });
-      extensionManager.loadExtensions();
-      extensionManager.disableExtension(
+      await extensionManager.loadExtensions();
+      await extensionManager.disableExtension(
         'disabled-extension',
         SettingScope.User,
       );
@@ -233,7 +273,7 @@ describe('extension tests', () => {
       expect(extensions[1].isActive).toBe(true);
     });
 
-    it('should hydrate variables', () => {
+    it('should hydrate variables', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'test-extension',
@@ -247,7 +287,7 @@ describe('extension tests', () => {
         },
       });
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
       expect(extensions).toHaveLength(1);
       const expectedCwd = path.join(
         userExtensionsDir,
@@ -266,7 +306,7 @@ describe('extension tests', () => {
       });
       fs.writeFileSync(path.join(sourceExtDir, 'context.md'), 'linked context');
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       const extension = await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'link',
@@ -303,7 +343,7 @@ describe('extension tests', () => {
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'link',
@@ -319,7 +359,7 @@ describe('extension tests', () => {
       ]);
     });
 
-    it('should resolve environment variables in extension configuration', () => {
+    it('should resolve environment variables in extension configuration', async () => {
       process.env['TEST_API_KEY'] = 'test-api-key-123';
       process.env['TEST_DB_URL'] = 'postgresql://localhost:5432/testdb';
 
@@ -352,7 +392,7 @@ describe('extension tests', () => {
         };
         fs.writeFileSync(configPath, JSON.stringify(extensionConfig));
 
-        const extensions = extensionManager.loadExtensions();
+        const extensions = await extensionManager.loadExtensions();
 
         expect(extensions).toHaveLength(1);
         const extension = extensions[0];
@@ -373,7 +413,7 @@ describe('extension tests', () => {
       }
     });
 
-    it('should resolve environment variables from an extension .env file', () => {
+    it('should resolve environment variables from an extension .env file', async () => {
       const extDir = createExtension({
         extensionsDir: userExtensionsDir,
         name: 'test-extension',
@@ -388,12 +428,19 @@ describe('extension tests', () => {
             },
           },
         },
+        settings: [
+          {
+            name: 'My API Key',
+            description: 'API key for testing.',
+            envVar: 'MY_API_KEY',
+          },
+        ],
       });
 
       const envFilePath = path.join(extDir, '.env');
       fs.writeFileSync(envFilePath, 'MY_API_KEY=test-key-from-file\n');
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(1);
       const extension = extensions[0];
@@ -403,7 +450,7 @@ describe('extension tests', () => {
       expect(serverConfig.env!['STATIC_VALUE']).toBe('no-substitution');
     });
 
-    it('should handle missing environment variables gracefully', () => {
+    it('should handle missing environment variables gracefully', async () => {
       const userExtensionsDir = path.join(
         tempHomeDir,
         EXTENSIONS_DIRECTORY_NAME,
@@ -433,7 +480,7 @@ describe('extension tests', () => {
         JSON.stringify(extensionConfig),
       );
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(1);
       const extension = extensions[0];
@@ -443,7 +490,7 @@ describe('extension tests', () => {
       expect(serverConfig.env!['MISSING_VAR_BRACES']).toBe('${ALSO_UNDEFINED}');
     });
 
-    it('should skip extensions with invalid JSON and log a warning', () => {
+    it('should skip extensions with invalid JSON and log a warning', async () => {
       const consoleSpy = vi
         .spyOn(console, 'error')
         .mockImplementation(() => {});
@@ -461,7 +508,7 @@ describe('extension tests', () => {
       const badConfigPath = path.join(badExtDir, EXTENSIONS_CONFIG_FILENAME);
       fs.writeFileSync(badConfigPath, '{ "name": "bad-ext"'); // Malformed
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(1);
       expect(extensions[0].name).toBe('good-ext');
@@ -474,7 +521,7 @@ describe('extension tests', () => {
       consoleSpy.mockRestore();
     });
 
-    it('should skip extensions with missing name and log a warning', () => {
+    it('should skip extensions with missing name and log a warning', async () => {
       const consoleSpy = vi
         .spyOn(console, 'error')
         .mockImplementation(() => {});
@@ -492,7 +539,7 @@ describe('extension tests', () => {
       const badConfigPath = path.join(badExtDir, EXTENSIONS_CONFIG_FILENAME);
       fs.writeFileSync(badConfigPath, JSON.stringify({ version: '1.0.0' }));
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
 
       expect(extensions).toHaveLength(1);
       expect(extensions[0].name).toBe('good-ext');
@@ -505,7 +552,7 @@ describe('extension tests', () => {
       consoleSpy.mockRestore();
     });
 
-    it('should filter trust out of mcp servers', () => {
+    it('should filter trust out of mcp servers', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'test-extension',
@@ -519,12 +566,12 @@ describe('extension tests', () => {
         },
       });
 
-      const extensions = extensionManager.loadExtensions();
+      const extensions = await extensionManager.loadExtensions();
       expect(extensions).toHaveLength(1);
       expect(extensions[0].mcpServers?.['test-server'].trust).toBeUndefined();
     });
 
-    it('should throw an error for invalid extension names', () => {
+    it('should throw an error for invalid extension names', async () => {
       const consoleSpy = vi
         .spyOn(console, 'error')
         .mockImplementation(() => {});
@@ -533,10 +580,8 @@ describe('extension tests', () => {
         name: 'bad_name',
         version: '1.0.0',
       });
-
-      const extension = extensionManager
-        .loadExtensions()
-        .find((e) => e.name === 'bad_name');
+      const extensions = await extensionManager.loadExtensions();
+      const extension = extensions.find((e) => e.name === 'bad_name');
 
       expect(extension).toBeUndefined();
       expect(consoleSpy).toHaveBeenCalledWith(
@@ -546,7 +591,7 @@ describe('extension tests', () => {
     });
 
     describe('id generation', () => {
-      it('should generate id from source for non-github git urls', () => {
+      it('should generate id from source for non-github git urls', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'my-ext',
@@ -556,14 +601,12 @@ describe('extension tests', () => {
             source: 'http://somehost.com/foo/bar',
           },
         });
-
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'my-ext');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'my-ext');
         expect(extension?.id).toBe(hashValue('http://somehost.com/foo/bar'));
       });
 
-      it('should generate id from owner/repo for github http urls', () => {
+      it('should generate id from owner/repo for github http urls', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'my-ext',
@@ -574,13 +617,12 @@ describe('extension tests', () => {
           },
         });
 
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'my-ext');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'my-ext');
         expect(extension?.id).toBe(hashValue('https://github.com/foo/bar'));
       });
 
-      it('should generate id from owner/repo for github ssh urls', () => {
+      it('should generate id from owner/repo for github ssh urls', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'my-ext',
@@ -591,13 +633,12 @@ describe('extension tests', () => {
           },
         });
 
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'my-ext');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'my-ext');
         expect(extension?.id).toBe(hashValue('https://github.com/foo/bar'));
       });
 
-      it('should generate id from source for github-release extension', () => {
+      it('should generate id from source for github-release extension', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'my-ext',
@@ -607,14 +648,12 @@ describe('extension tests', () => {
             source: 'https://github.com/foo/bar',
           },
         });
-
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'my-ext');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'my-ext');
         expect(extension?.id).toBe(hashValue('https://github.com/foo/bar'));
       });
 
-      it('should generate id from the original source for local extension', () => {
+      it('should generate id from the original source for local extension', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'local-ext-name',
@@ -625,9 +664,8 @@ describe('extension tests', () => {
           },
         });
 
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'local-ext-name');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'local-ext-name');
         expect(extension?.id).toBe(hashValue('/some/path'));
       });
 
@@ -638,7 +676,7 @@ describe('extension tests', () => {
           name: 'link-ext-name',
           version: '1.0.0',
         });
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.installOrUpdateExtension({
           type: 'link',
           source: actualExtensionDir,
@@ -650,16 +688,15 @@ describe('extension tests', () => {
         expect(extension?.id).toBe(hashValue(actualExtensionDir));
       });
 
-      it('should generate id from name for extension with no install metadata', () => {
+      it('should generate id from name for extension with no install metadata', async () => {
         createExtension({
           extensionsDir: userExtensionsDir,
           name: 'no-meta-name',
           version: '1.0.0',
         });
 
-        const extension = extensionManager
-          .loadExtensions()
-          .find((e) => e.name === 'no-meta-name');
+        const extensions = await extensionManager.loadExtensions();
+        const extension = extensions.find((e) => e.name === 'no-meta-name');
         expect(extension?.id).toBe(hashValue('no-meta-name'));
       });
     });
@@ -675,7 +712,7 @@ describe('extension tests', () => {
       const targetExtDir = path.join(userExtensionsDir, 'my-local-extension');
       const metadataPath = path.join(targetExtDir, INSTALL_METADATA_FILENAME);
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'local',
@@ -697,7 +734,7 @@ describe('extension tests', () => {
         name: 'my-local-extension',
         version: '1.0.0',
       });
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'local',
@@ -791,7 +828,7 @@ describe('extension tests', () => {
         type: 'github-release',
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: gitUrl,
         type: 'git',
@@ -816,7 +853,7 @@ describe('extension tests', () => {
       const metadataPath = path.join(targetExtDir, INSTALL_METADATA_FILENAME);
       const configPath = path.join(targetExtDir, EXTENSIONS_CONFIG_FILENAME);
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'link',
@@ -846,7 +883,7 @@ describe('extension tests', () => {
             name: 'my-local-extension',
             version: '1.1.0',
           });
-          extensionManager.loadExtensions();
+          await extensionManager.loadExtensions();
           if (isUpdate) {
             await extensionManager.installOrUpdateExtension({
               source: sourceExtDir,
@@ -920,7 +957,7 @@ describe('extension tests', () => {
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await expect(
         extensionManager.installOrUpdateExtension({
           source: sourceExtDir,
@@ -952,7 +989,7 @@ This extension will run the following MCP servers:
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await expect(
         extensionManager.installOrUpdateExtension({
           source: sourceExtDir,
@@ -974,7 +1011,7 @@ This extension will run the following MCP servers:
         },
       });
       mockRequestConsent.mockResolvedValue(false);
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await expect(
         extensionManager.installOrUpdateExtension({
           source: sourceExtDir,
@@ -992,7 +1029,7 @@ This extension will run the following MCP servers:
       const targetExtDir = path.join(userExtensionsDir, 'my-local-extension');
       const metadataPath = path.join(targetExtDir, INSTALL_METADATA_FILENAME);
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'local',
@@ -1023,7 +1060,7 @@ This extension will run the following MCP servers:
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       // Install it with hard coded consent first.
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
@@ -1058,7 +1095,7 @@ This extension will run the following MCP servers:
         ],
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'local',
@@ -1088,7 +1125,7 @@ This extension will run the following MCP servers:
         settings: loadSettings(tempWorkspaceDir).merged,
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: sourceExtDir,
         type: 'local',
@@ -1111,7 +1148,7 @@ This extension will run the following MCP servers:
       });
 
       mockPromptForSettings.mockResolvedValueOnce('old-api-key');
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       // Install it so it exists in the userExtensionsDir
       await extensionManager.installOrUpdateExtension({
         source: oldSourceExtDir,
@@ -1181,7 +1218,7 @@ This extension will run the following MCP servers:
           },
         ],
       });
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.installOrUpdateExtension({
         source: oldSourceExtDir,
         type: 'local',
@@ -1273,7 +1310,7 @@ This extension will run the following MCP servers:
           join(tempDir, extensionName),
         );
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.installOrUpdateExtension({
           source: gitUrl,
           type: 'github-release',
@@ -1298,7 +1335,7 @@ This extension will run the following MCP servers:
           type: 'github-release',
         });
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.installOrUpdateExtension(
           { source: gitUrl, type: 'github-release' }, // Use github-release to force consent
         );
@@ -1329,7 +1366,7 @@ This extension will run the following MCP servers:
         });
         mockRequestConsent.mockResolvedValue(false);
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await expect(
           extensionManager.installOrUpdateExtension({
             source: gitUrl,
@@ -1354,7 +1391,7 @@ This extension will run the following MCP servers:
           type: 'github-release',
         });
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.installOrUpdateExtension({
           source: gitUrl,
           type: 'git',
@@ -1385,7 +1422,7 @@ This extension will run the following MCP servers:
           type: 'github-release',
         });
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.installOrUpdateExtension(
           { source: gitUrl, type: 'github-release' }, // Note the type
         );
@@ -1407,8 +1444,7 @@ This extension will run the following MCP servers:
         name: 'my-local-extension',
         version: '1.0.0',
       });
-
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.uninstallExtension('my-local-extension', false);
 
       expect(fs.existsSync(sourceExtDir)).toBe(false);
@@ -1426,7 +1462,7 @@ This extension will run the following MCP servers:
         version: '1.0.0',
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.uninstallExtension('my-local-extension', false);
 
       expect(fs.existsSync(sourceExtDir)).toBe(false);
@@ -1435,7 +1471,7 @@ This extension will run the following MCP servers:
     });
 
     it('should throw an error if the extension does not exist', async () => {
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await expect(
         extensionManager.uninstallExtension('nonexistent-extension', false),
       ).rejects.toThrow('Extension not found.');
@@ -1453,7 +1489,7 @@ This extension will run the following MCP servers:
           },
         });
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.uninstallExtension(
           'my-local-extension',
           isUpdate,
@@ -1481,7 +1517,7 @@ This extension will run the following MCP servers:
         const enablementManager = new ExtensionEnablementManager();
         enablementManager.enable('test-extension', true, '/some/scope');
 
-        extensionManager.loadExtensions();
+        await extensionManager.loadExtensions();
         await extensionManager.uninstallExtension('test-extension', isUpdate);
 
         const config = enablementManager.readConfig()['test-extension'];
@@ -1506,7 +1542,7 @@ This extension will run the following MCP servers:
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await extensionManager.uninstallExtension(gitUrl, false);
 
       expect(fs.existsSync(sourceExtDir)).toBe(false);
@@ -1526,7 +1562,7 @@ This extension will run the following MCP servers:
         // No installMetadata provided
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       await expect(
         extensionManager.uninstallExtension(
           'https://github.com/google/no-metadata-extension',
@@ -1537,14 +1573,14 @@ This extension will run the following MCP servers:
   });
 
   describe('disableExtension', () => {
-    it('should disable an extension at the user scope', () => {
+    it('should disable an extension at the user scope', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'my-extension',
         version: '1.0.0',
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('my-extension', SettingScope.User);
       expect(
         isEnabled({
@@ -1554,14 +1590,14 @@ This extension will run the following MCP servers:
       ).toBe(false);
     });
 
-    it('should disable an extension at the workspace scope', () => {
+    it('should disable an extension at the workspace scope', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'my-extension',
         version: '1.0.0',
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('my-extension', SettingScope.Workspace);
       expect(
         isEnabled({
@@ -1577,14 +1613,14 @@ This extension will run the following MCP servers:
       ).toBe(false);
     });
 
-    it('should handle disabling the same extension twice', () => {
+    it('should handle disabling the same extension twice', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'my-extension',
         version: '1.0.0',
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('my-extension', SettingScope.User);
       extensionManager.disableExtension('my-extension', SettingScope.User);
       expect(
@@ -1595,13 +1631,17 @@ This extension will run the following MCP servers:
       ).toBe(false);
     });
 
-    it('should throw an error if you request system scope', () => {
-      expect(() =>
-        extensionManager.disableExtension('my-extension', SettingScope.System),
-      ).toThrow('System and SystemDefaults scopes are not supported.');
+    it('should throw an error if you request system scope', async () => {
+      await expect(
+        async () =>
+          await extensionManager.disableExtension(
+            'my-extension',
+            SettingScope.System,
+          ),
+      ).rejects.toThrow('System and SystemDefaults scopes are not supported.');
     });
 
-    it('should log a disable event', () => {
+    it('should log a disable event', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
@@ -1612,7 +1652,7 @@ This extension will run the following MCP servers:
         },
       });
 
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('ext1', SettingScope.Workspace);
 
       expect(mockLogExtensionDisable).toHaveBeenCalled();
@@ -1634,41 +1674,41 @@ This extension will run the following MCP servers:
       return extensions.filter((e) => e.isActive);
     };
 
-    it('should enable an extension at the user scope', () => {
+    it('should enable an extension at the user scope', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
         version: '1.0.0',
       });
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('ext1', SettingScope.User);
       let activeExtensions = getActiveExtensions();
       expect(activeExtensions).toHaveLength(0);
 
-      extensionManager.enableExtension('ext1', SettingScope.User);
-      activeExtensions = getActiveExtensions();
+      await extensionManager.enableExtension('ext1', SettingScope.User);
+      activeExtensions = await getActiveExtensions();
       expect(activeExtensions).toHaveLength(1);
       expect(activeExtensions[0].name).toBe('ext1');
     });
 
-    it('should enable an extension at the workspace scope', () => {
+    it('should enable an extension at the workspace scope', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
         version: '1.0.0',
       });
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('ext1', SettingScope.Workspace);
       let activeExtensions = getActiveExtensions();
       expect(activeExtensions).toHaveLength(0);
 
-      extensionManager.enableExtension('ext1', SettingScope.Workspace);
-      activeExtensions = getActiveExtensions();
+      await extensionManager.enableExtension('ext1', SettingScope.Workspace);
+      activeExtensions = await getActiveExtensions();
       expect(activeExtensions).toHaveLength(1);
       expect(activeExtensions[0].name).toBe('ext1');
     });
 
-    it('should log an enable event', () => {
+    it('should log an enable event', async () => {
       createExtension({
         extensionsDir: userExtensionsDir,
         name: 'ext1',
@@ -1678,7 +1718,7 @@ This extension will run the following MCP servers:
           type: 'local',
         },
       });
-      extensionManager.loadExtensions();
+      await extensionManager.loadExtensions();
       extensionManager.disableExtension('ext1', SettingScope.Workspace);
       extensionManager.enableExtension('ext1', SettingScope.Workspace);
 

packages/cli/src/config/extensions/extensionSettings.test.ts

@@ -17,6 +17,7 @@ import { ExtensionStorage } from './storage.js';
 import prompts from 'prompts';
 import * as fsPromises from 'node:fs/promises';
 import * as fs from 'node:fs';
+import { KeychainTokenStorage } from '@google/gemini-cli-core';
 
 vi.mock('prompts');
 vi.mock('os', async (importOriginal) => {
@@ -27,11 +28,59 @@ vi.mock('os', async (importOriginal) => {
   };
 });
 
+vi.mock('@google/gemini-cli-core', async (importOriginal) => {
+  const actual =
+    await importOriginal<typeof import('@google/gemini-cli-core')>();
+  return {
+    ...actual,
+    KeychainTokenStorage: vi.fn().mockImplementation(() => ({
+      getSecret: vi.fn(),
+      setSecret: vi.fn(),
+      deleteSecret: vi.fn(),
+      listSecrets: vi.fn(),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    })),
+  };
+});
+
+interface MockKeychainStorage {
+  getSecret: ReturnType<typeof vi.fn>;
+  setSecret: ReturnType<typeof vi.fn>;
+  deleteSecret: ReturnType<typeof vi.fn>;
+  listSecrets: ReturnType<typeof vi.fn>;
+  isAvailable: ReturnType<typeof vi.fn>;
+}
+
 describe('extensionSettings', () => {
   let tempHomeDir: string;
   let extensionDir: string;
+  let mockKeychainStorage: MockKeychainStorage;
+  let keychainData: Record<string, string>;
 
   beforeEach(() => {
+    vi.clearAllMocks();
+    keychainData = {};
+    mockKeychainStorage = {
+      getSecret: vi
+        .fn()
+        .mockImplementation(async (key: string) => keychainData[key] || null),
+      setSecret: vi
+        .fn()
+        .mockImplementation(async (key: string, value: string) => {
+          keychainData[key] = value;
+        }),
+      deleteSecret: vi.fn().mockImplementation(async (key: string) => {
+        delete keychainData[key];
+      }),
+      listSecrets: vi
+        .fn()
+        .mockImplementation(async () => Object.keys(keychainData)),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    };
+    (
+      KeychainTokenStorage as unknown as ReturnType<typeof vi.fn>
+    ).mockImplementation(() => mockKeychainStorage);
+
     tempHomeDir = os.tmpdir() + path.sep + `gemini-cli-test-home-${Date.now()}`;
     extensionDir = path.join(tempHomeDir, '.gemini', 'extensions', 'test-ext');
     // Spy and mock the method, but also create the directory so we can write to it.
@@ -59,7 +108,13 @@ describe('extensionSettings', () => {
 
     it('should do nothing if settings are undefined', async () => {
       const config: ExtensionConfig = { name: 'test-ext', version: '1.0.0' };
-      await maybePromptForSettings(config, mockRequestSetting);
+      await maybePromptForSettings(
+        config,
+        '12345',
+        mockRequestSetting,
+        undefined,
+        undefined,
+      );
       expect(mockRequestSetting).not.toHaveBeenCalled();
     });
 
@@ -69,11 +124,17 @@ describe('extensionSettings', () => {
         version: '1.0.0',
         settings: [],
       };
-      await maybePromptForSettings(config, mockRequestSetting);
+      await maybePromptForSettings(
+        config,
+        '12345',
+        mockRequestSetting,
+        undefined,
+        undefined,
+      );
       expect(mockRequestSetting).not.toHaveBeenCalled();
     });
 
-    it('should call requestSetting for each setting', async () => {
+    it('should prompt for all settings if there is no previous config', async () => {
       const config: ExtensionConfig = {
         name: 'test-ext',
         version: '1.0.0',
@@ -82,14 +143,25 @@ describe('extensionSettings', () => {
           { name: 's2', description: 'd2', envVar: 'VAR2' },
         ],
       };
-      await maybePromptForSettings(config, mockRequestSetting);
+      await maybePromptForSettings(
+        config,
+        '12345',
+        mockRequestSetting,
+        undefined,
+        undefined,
+      );
       expect(mockRequestSetting).toHaveBeenCalledTimes(2);
       expect(mockRequestSetting).toHaveBeenCalledWith(config.settings![0]);
       expect(mockRequestSetting).toHaveBeenCalledWith(config.settings![1]);
     });
 
-    it('should write the .env file with the correct content', async () => {
-      const config: ExtensionConfig = {
+    it('should only prompt for new settings', async () => {
+      const previousConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [{ name: 's1', description: 'd1', envVar: 'VAR1' }],
+      };
+      const newConfig: ExtensionConfig = {
         name: 'test-ext',
         version: '1.0.0',
         settings: [
@@ -97,35 +169,151 @@ describe('extensionSettings', () => {
           { name: 's2', description: 'd2', envVar: 'VAR2' },
         ],
       };
-      await maybePromptForSettings(config, mockRequestSetting);
+      const previousSettings = { VAR1: 'previous-VAR1' };
+
+      await maybePromptForSettings(
+        newConfig,
+        '12345',
+        mockRequestSetting,
+        previousConfig,
+        previousSettings,
+      );
+
+      expect(mockRequestSetting).toHaveBeenCalledTimes(1);
+      expect(mockRequestSetting).toHaveBeenCalledWith(newConfig.settings![1]);
 
       const expectedEnvPath = path.join(extensionDir, '.env');
       const actualContent = await fsPromises.readFile(expectedEnvPath, 'utf-8');
-      const expectedContent = 'VAR1=mock-VAR1\nVAR2=mock-VAR2\n';
+      const expectedContent = 'VAR1=previous-VAR1\nVAR2=mock-VAR2\n';
+      expect(actualContent).toBe(expectedContent);
+    });
 
+    it('should remove settings that are no longer in the config', async () => {
+      const previousConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [
+          { name: 's1', description: 'd1', envVar: 'VAR1' },
+          { name: 's2', description: 'd2', envVar: 'VAR2' },
+        ],
+      };
+      const newConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [{ name: 's1', description: 'd1', envVar: 'VAR1' }],
+      };
+      const previousSettings = {
+        VAR1: 'previous-VAR1',
+        VAR2: 'previous-VAR2',
+      };
+
+      await maybePromptForSettings(
+        newConfig,
+        '12345',
+        mockRequestSetting,
+        previousConfig,
+        previousSettings,
+      );
+
+      expect(mockRequestSetting).not.toHaveBeenCalled();
+
+      const expectedEnvPath = path.join(extensionDir, '.env');
+      const actualContent = await fsPromises.readFile(expectedEnvPath, 'utf-8');
+      const expectedContent = 'VAR1=previous-VAR1\n';
+      expect(actualContent).toBe(expectedContent);
+    });
+
+    it('should reprompt if a setting changes sensitivity', async () => {
+      const previousConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [
+          { name: 's1', description: 'd1', envVar: 'VAR1', sensitive: false },
+        ],
+      };
+      const newConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [
+          { name: 's1', description: 'd1', envVar: 'VAR1', sensitive: true },
+        ],
+      };
+      const previousSettings = { VAR1: 'previous-VAR1' };
+
+      await maybePromptForSettings(
+        newConfig,
+        '12345',
+        mockRequestSetting,
+        previousConfig,
+        previousSettings,
+      );
+
+      expect(mockRequestSetting).toHaveBeenCalledTimes(1);
+      expect(mockRequestSetting).toHaveBeenCalledWith(newConfig.settings![0]);
+
+      // The value should now be in keychain, not the .env file.
+      const expectedEnvPath = path.join(extensionDir, '.env');
+      const actualContent = await fsPromises.readFile(expectedEnvPath, 'utf-8');
+      expect(actualContent).toBe('');
+    });
+
+    it('should not prompt if settings are identical', async () => {
+      const previousConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [
+          { name: 's1', description: 'd1', envVar: 'VAR1' },
+          { name: 's2', description: 'd2', envVar: 'VAR2' },
+        ],
+      };
+      const newConfig: ExtensionConfig = {
+        name: 'test-ext',
+        version: '1.0.0',
+        settings: [
+          { name: 's1', description: 'd1', envVar: 'VAR1' },
+          { name: 's2', description: 'd2', envVar: 'VAR2' },
+        ],
+      };
+      const previousSettings = {
+        VAR1: 'previous-VAR1',
+        VAR2: 'previous-VAR2',
+      };
+
+      await maybePromptForSettings(
+        newConfig,
+        '12345',
+        mockRequestSetting,
+        previousConfig,
+        previousSettings,
+      );
+
+      expect(mockRequestSetting).not.toHaveBeenCalled();
+      const expectedEnvPath = path.join(extensionDir, '.env');
+      const actualContent = await fsPromises.readFile(expectedEnvPath, 'utf-8');
+      const expectedContent = 'VAR1=previous-VAR1\nVAR2=previous-VAR2\n';
       expect(actualContent).toBe(expectedContent);
     });
   });
 
   describe('promptForSetting', () => {
-    // it('should use prompts with type "password" for sensitive settings', async () => {
-    //   const setting: ExtensionSetting = {
-    //     name: 'API Key',
-    //     description: 'Your secret key',
-    //     envVar: 'API_KEY',
-    //     sensitive: true,
-    //   };
-    //   vi.mocked(prompts).mockResolvedValue({ value: 'secret-key' });
+    it('should use prompts with type "password" for sensitive settings', async () => {
+      const setting: ExtensionSetting = {
+        name: 'API Key',
+        description: 'Your secret key',
+        envVar: 'API_KEY',
+        sensitive: true,
+      };
+      vi.mocked(prompts).mockResolvedValue({ value: 'secret-key' });
 
-    //   const result = await promptForSetting(setting);
+      const result = await promptForSetting(setting);
 
-    //   expect(prompts).toHaveBeenCalledWith({
-    //     type: 'password',
-    //     name: 'value',
-    //     message: 'API Key\nYour secret key',
-    //   });
-    //   expect(result).toBe('secret-key');
-    // });
+      expect(prompts).toHaveBeenCalledWith({
+        type: 'password',
+        name: 'value',
+        message: 'API Key\nYour secret key',
+      });
+      expect(result).toBe('secret-key');
+    });
 
     it('should use prompts with type "text" for non-sensitive settings', async () => {
       const setting: ExtensionSetting = {

packages/cli/src/config/extensions/extensionSettings.ts

@@ -12,57 +12,76 @@ import { ExtensionStorage } from './storage.js';
 import type { ExtensionConfig } from '../extension.js';
 
 import prompts from 'prompts';
+import { KeychainTokenStorage } from '@google/gemini-cli-core';
 
 export interface ExtensionSetting {
   name: string;
   description: string;
   envVar: string;
+  // NOTE: If no value is set, this setting will be considered NOT sensitive.
+  sensitive?: boolean;
 }
 
 export async function maybePromptForSettings(
   extensionConfig: ExtensionConfig,
+  extensionId: string,
   requestSetting: (setting: ExtensionSetting) => Promise<string>,
   previousExtensionConfig?: ExtensionConfig,
   previousSettings?: Record<string, string>,
 ): Promise<void> {
   const { name: extensionName, settings } = extensionConfig;
+  if (
+    (!settings || settings.length === 0) &&
+    (!previousExtensionConfig?.settings ||
+      previousExtensionConfig.settings.length === 0)
+  ) {
+    return;
+  }
   const envFilePath = new ExtensionStorage(extensionName).getEnvFilePath();
+  const keychain = new KeychainTokenStorage(extensionId);
 
   if (!settings || settings.length === 0) {
-    // No settings for this extension. Clear any existing .env file.
-    if (fsSync.existsSync(envFilePath)) {
-      await fs.writeFile(envFilePath, '');
-    }
+    await clearSettings(envFilePath, keychain);
     return;
   }
 
-  let settingsToPrompt = settings;
-  if (previousExtensionConfig) {
-    const oldSettings = new Set(
-      previousExtensionConfig.settings?.map((s) => s.name) || [],
-    );
-    settingsToPrompt = settingsToPrompt.filter((s) => !oldSettings.has(s.name));
-  }
+  const settingsChanges = getSettingsChanges(
+    settings,
+    previousExtensionConfig?.settings ?? [],
+  );
 
   const allSettings: Record<string, string> = { ...(previousSettings ?? {}) };
 
-  if (settingsToPrompt && settingsToPrompt.length > 0) {
-    for (const setting of settingsToPrompt) {
-      const answer = await requestSetting(setting);
-      allSettings[setting.envVar] = answer;
-    }
+  for (const removedEnvSetting of settingsChanges.removeEnv) {
+    delete allSettings[removedEnvSetting.envVar];
   }
 
-  const validEnvVars = new Set(settings.map((s) => s.envVar));
-  const finalSettings: Record<string, string> = {};
-  for (const [key, value] of Object.entries(allSettings)) {
-    if (validEnvVars.has(key)) {
-      finalSettings[key] = value;
+  for (const removedSensitiveSetting of settingsChanges.removeSensitive) {
+    await keychain.deleteSecret(removedSensitiveSetting.envVar);
+  }
+
+  for (const setting of settingsChanges.promptForSensitive.concat(
+    settingsChanges.promptForEnv,
+  )) {
+    const answer = await requestSetting(setting);
+    allSettings[setting.envVar] = answer;
+  }
+
+  const nonSensitiveSettings: Record<string, string> = {};
+  for (const setting of settings) {
+    const value = allSettings[setting.envVar];
+    if (value === undefined) {
+      continue;
+    }
+    if (setting.sensitive) {
+      await keychain.setSecret(setting.envVar, value);
+    } else {
+      nonSensitiveSettings[setting.envVar] = value;
     }
   }
 
   let envContent = '';
-  for (const [key, value] of Object.entries(finalSettings)) {
+  for (const [key, value] of Object.entries(nonSensitiveSettings)) {
     envContent += `${key}=${value}\n`;
   }
 
@@ -73,17 +92,22 @@ export async function promptForSetting(
   setting: ExtensionSetting,
 ): Promise<string> {
   const response = await prompts({
-    // type: setting.sensitive ? 'password' : 'text',
-    type: 'text',
+    type: setting.sensitive ? 'password' : 'text',
     name: 'value',
     message: `${setting.name}\n${setting.description}`,
   });
   return response.value;
 }
 
-export function getEnvContents(
-  extensionStorage: ExtensionStorage,
-): Record<string, string> {
+export async function getEnvContents(
+  extensionConfig: ExtensionConfig,
+  extensionId: string,
+): Promise<Record<string, string>> {
+  if (!extensionConfig.settings || extensionConfig.settings.length === 0) {
+    return Promise.resolve({});
+  }
+  const extensionStorage = new ExtensionStorage(extensionConfig.name);
+  const keychain = new KeychainTokenStorage(extensionId);
   let customEnv: Record<string, string> = {};
   if (fsSync.existsSync(extensionStorage.getEnvFilePath())) {
     const envFile = fsSync.readFileSync(
@@ -92,5 +116,67 @@ export function getEnvContents(
     );
     customEnv = dotenv.parse(envFile);
   }
+
+  if (extensionConfig.settings) {
+    for (const setting of extensionConfig.settings) {
+      if (setting.sensitive) {
+        const secret = await keychain.getSecret(setting.envVar);
+        if (secret) {
+          customEnv[setting.envVar] = secret;
+        }
+      }
+    }
+  }
   return customEnv;
 }
+
+interface settingsChanges {
+  promptForSensitive: ExtensionSetting[];
+  removeSensitive: ExtensionSetting[];
+  promptForEnv: ExtensionSetting[];
+  removeEnv: ExtensionSetting[];
+}
+function getSettingsChanges(
+  settings: ExtensionSetting[],
+  oldSettings: ExtensionSetting[],
+): settingsChanges {
+  const isSameSetting = (a: ExtensionSetting, b: ExtensionSetting) =>
+    a.envVar === b.envVar && (a.sensitive ?? false) === (b.sensitive ?? false);
+
+  const sensitiveOld = oldSettings.filter((s) => s.sensitive ?? false);
+  const sensitiveNew = settings.filter((s) => s.sensitive ?? false);
+  const envOld = oldSettings.filter((s) => !(s.sensitive ?? false));
+  const envNew = settings.filter((s) => !(s.sensitive ?? false));
+
+  return {
+    promptForSensitive: sensitiveNew.filter(
+      (s) => !sensitiveOld.some((old) => isSameSetting(s, old)),
+    ),
+    removeSensitive: sensitiveOld.filter(
+      (s) => !sensitiveNew.some((neu) => isSameSetting(s, neu)),
+    ),
+    promptForEnv: envNew.filter(
+      (s) => !envOld.some((old) => isSameSetting(s, old)),
+    ),
+    removeEnv: envOld.filter(
+      (s) => !envNew.some((neu) => isSameSetting(s, neu)),
+    ),
+  };
+}
+
+async function clearSettings(
+  envFilePath: string,
+  keychain: KeychainTokenStorage,
+) {
+  if (fsSync.existsSync(envFilePath)) {
+    await fs.writeFile(envFilePath, '');
+  }
+  if (!keychain.isAvailable()) {
+    return;
+  }
+  const secrets = await keychain.listSecrets();
+  for (const secret of secrets) {
+    await keychain.deleteSecret(secret);
+  }
+  return;
+}

packages/cli/src/config/extensions/update.test.ts

@@ -9,7 +9,7 @@ import * as fs from 'node:fs';
 import * as os from 'node:os';
 import * as path from 'node:path';
 import { checkForAllExtensionUpdates, updateExtension } from './update.js';
-import { GEMINI_DIR } from '@google/gemini-cli-core';
+import { GEMINI_DIR, KeychainTokenStorage } from '@google/gemini-cli-core';
 import { isWorkspaceTrusted } from '../trustedFolders.js';
 import { ExtensionUpdateState } from '../../ui/state/extensions.js';
 import { createExtension } from '../../test-utils/createExtension.js';
@@ -64,9 +64,24 @@ vi.mock('@google/gemini-cli-core', async (importOriginal) => {
     logExtensionUninstall: mockLogExtensionUninstall,
     ExtensionInstallEvent: vi.fn(),
     ExtensionUninstallEvent: vi.fn(),
+    KeychainTokenStorage: vi.fn().mockImplementation(() => ({
+      getSecret: vi.fn(),
+      setSecret: vi.fn(),
+      deleteSecret: vi.fn(),
+      listSecrets: vi.fn(),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    })),
   };
 });
 
+interface MockKeychainStorage {
+  getSecret: ReturnType<typeof vi.fn>;
+  setSecret: ReturnType<typeof vi.fn>;
+  deleteSecret: ReturnType<typeof vi.fn>;
+  listSecrets: ReturnType<typeof vi.fn>;
+  isAvailable: ReturnType<typeof vi.fn>;
+}
+
 describe('update tests', () => {
   let tempHomeDir: string;
   let tempWorkspaceDir: string;
@@ -76,8 +91,32 @@ describe('update tests', () => {
   let mockPromptForSettings: MockedFunction<
     (setting: ExtensionSetting) => Promise<string>
   >;
+  let mockKeychainStorage: MockKeychainStorage;
+  let keychainData: Record<string, string>;
 
   beforeEach(() => {
+    vi.clearAllMocks();
+    keychainData = {};
+    mockKeychainStorage = {
+      getSecret: vi
+        .fn()
+        .mockImplementation(async (key: string) => keychainData[key] || null),
+      setSecret: vi
+        .fn()
+        .mockImplementation(async (key: string, value: string) => {
+          keychainData[key] = value;
+        }),
+      deleteSecret: vi.fn().mockImplementation(async (key: string) => {
+        delete keychainData[key];
+      }),
+      listSecrets: vi
+        .fn()
+        .mockImplementation(async () => Object.keys(keychainData)),
+      isAvailable: vi.fn().mockResolvedValue(true),
+    };
+    (
+      KeychainTokenStorage as unknown as ReturnType<typeof vi.fn>
+    ).mockImplementation(() => mockKeychainStorage);
     tempHomeDir = fs.mkdtempSync(
       path.join(os.tmpdir(), 'gemini-cli-test-home-'),
     );
@@ -110,6 +149,7 @@ describe('update tests', () => {
   afterEach(() => {
     fs.rmSync(tempHomeDir, { recursive: true, force: true });
     fs.rmSync(tempWorkspaceDir, { recursive: true, force: true });
+    vi.restoreAllMocks();
   });
 
   describe('updateExtension', () => {
@@ -139,11 +179,10 @@ describe('update tests', () => {
         );
       });
       mockGit.getRemotes.mockResolvedValue([{ name: 'origin' }]);
-      const extension = extensionManager
-        .loadExtensions()
-        .find((e) => e.name === extensionName)!;
+      const extensions = await extensionManager.loadExtensions();
+      const extension = extensions.find((e) => e.name === extensionName)!;
       const updateInfo = await updateExtension(
-        extension,
+        extension!,
         extensionManager,
         ExtensionUpdateState.UPDATE_AVAILABLE,
         () => {},
@@ -189,11 +228,10 @@ describe('update tests', () => {
 
       const dispatch = vi.fn();
 
-      const extension = extensionManager
-        .loadExtensions()
-        .find((e) => e.name === extensionName)!;
+      const extensions = await extensionManager.loadExtensions();
+      const extension = extensions.find((e) => e.name === extensionName)!;
       await updateExtension(
-        extension,
+        extension!,
         extensionManager,
         ExtensionUpdateState.UPDATE_AVAILABLE,
         dispatch,
@@ -231,12 +269,11 @@ describe('update tests', () => {
       mockGit.getRemotes.mockResolvedValue([{ name: 'origin' }]);
 
       const dispatch = vi.fn();
-      const extension = extensionManager
-        .loadExtensions()
-        .find((e) => e.name === extensionName)!;
+      const extensions = await extensionManager.loadExtensions();
+      const extension = extensions.find((e) => e.name === extensionName)!;
       await expect(
         updateExtension(
-          extension,
+          extension!,
           extensionManager,
           ExtensionUpdateState.UPDATE_AVAILABLE,
           dispatch,
@@ -280,7 +317,7 @@ describe('update tests', () => {
 
       const dispatch = vi.fn();
       await checkForAllExtensionUpdates(
-        extensionManager.loadExtensions(),
+        await extensionManager.loadExtensions(),
         extensionManager,
         dispatch,
       );
@@ -312,7 +349,7 @@ describe('update tests', () => {
 
       const dispatch = vi.fn();
       await checkForAllExtensionUpdates(
-        extensionManager.loadExtensions(),
+        await extensionManager.loadExtensions(),
         extensionManager,
         dispatch,
       );
@@ -341,7 +378,7 @@ describe('update tests', () => {
       });
       const dispatch = vi.fn();
       await checkForAllExtensionUpdates(
-        extensionManager.loadExtensions(),
+        await extensionManager.loadExtensions(),
         extensionManager,
         dispatch,
       );
@@ -370,7 +407,7 @@ describe('update tests', () => {
       });
       const dispatch = vi.fn();
       await checkForAllExtensionUpdates(
-        extensionManager.loadExtensions(),
+        await extensionManager.loadExtensions(),
         extensionManager,
         dispatch,
       );
@@ -398,7 +435,7 @@ describe('update tests', () => {
 
       const dispatch = vi.fn();
       await checkForAllExtensionUpdates(
-        extensionManager.loadExtensions(),
+        await extensionManager.loadExtensions(),
         extensionManager,
         dispatch,
       );

packages/cli/src/config/extensions/update.ts

@@ -58,7 +58,7 @@ export async function updateExtension(
 
   const tempDir = await ExtensionStorage.createTmpDir();
   try {
-    const previousExtensionConfig = await extensionManager.loadExtensionConfig(
+    const previousExtensionConfig = extensionManager.loadExtensionConfig(
       extension.path,
     );
     let updatedExtension: GeminiCLIExtension;

packages/cli/src/config/settings.test.ts

@@ -2442,7 +2442,7 @@ describe('Settings Loading and Merging', () => {
         extensionManager,
         'disableExtension',
       );
-      mockDisableExtension.mockImplementation(() => {});
+      mockDisableExtension.mockImplementation(async () => {});
 
       migrateDeprecatedSettings(loadedSettings, extensionManager);
 
@@ -2515,7 +2515,7 @@ describe('Settings Loading and Merging', () => {
         extensionManager,
         'disableExtension',
       );
-      mockDisableExtension.mockImplementation(() => {});
+      mockDisableExtension.mockImplementation(async () => {});
 
       migrateDeprecatedSettings(loadedSettings, extensionManager);
 

packages/cli/src/ui/hooks/useExtensionUpdates.test.tsx

@@ -124,7 +124,7 @@ describe('useExtensionUpdates', () => {
         autoUpdate: true,
       },
     });
-
+    await extensionManager.loadExtensions();
     const addItem = vi.fn();
 
     vi.mocked(checkForAllExtensionUpdates).mockImplementation(
@@ -145,7 +145,6 @@ describe('useExtensionUpdates', () => {
       name: '',
     });
 
-    extensionManager.loadExtensions();
     function TestComponent() {
       useExtensionUpdates(extensionManager, addItem);
       return null;
@@ -189,7 +188,7 @@ describe('useExtensionUpdates', () => {
       },
     });
 
-    extensionManager.loadExtensions();
+    await extensionManager.loadExtensions();
 
     const addItem = vi.fn();