fix: auth refresh token (#1299)

Co-authored-by: github-actions[bot] <github-actions[bot]@users.noreply.github.com>

packages/tm-core/package.json

@@ -37,7 +37,8 @@
 		"@types/node": "^22.10.5",
 		"@vitest/coverage-v8": "^3.2.4",
 		"typescript": "^5.9.2",
-		"vitest": "^3.2.4"
+		"vitest": "^3.2.4",
+		"strip-literal": "3.1.0"
 	},
 	"files": ["src", "README.md", "CHANGELOG.md"],
 	"keywords": ["task-management", "typescript", "ai", "prd", "parser"],

packages/tm-core/src/auth/auth-manager.spec.ts

@@ -21,11 +21,16 @@ const CredentialStoreSpy = vi.fn();
 vi.mock('./credential-store.js', () => {
 	return {
 		CredentialStore: class {
+			static getInstance(config?: any) {
+				return new (this as any)(config);
+			}
+			static resetInstance() {
+				// Mock reset instance method
+			}
 			constructor(config: any) {
 				CredentialStoreSpy(config);
-				this.getCredentials = vi.fn(() => null);
 			}
-			getCredentials() {
+			getCredentials(_options?: any) {
 				return null;
 			}
 			saveCredentials() {}
@@ -85,7 +90,7 @@ describe('AuthManager Singleton', () => {
 		expect(instance1).toBe(instance2);
 	});
 
-	it('should use config on first call', () => {
+	it('should use config on first call', async () => {
 		const config = {
 			baseUrl: 'https://test.auth.com',
 			configDir: '/test/config',
@@ -101,7 +106,7 @@ describe('AuthManager Singleton', () => {
 
 		// Verify the config is passed to internal components through observable behavior
 		// getCredentials would look in the configured file path
-		const credentials = instance.getCredentials();
+		const credentials = await instance.getCredentials();
 		expect(credentials).toBeNull(); // File doesn't exist, but config was propagated correctly
 	});
 

packages/tm-core/src/auth/auth-manager.ts

@@ -29,6 +29,8 @@ export class AuthManager {
 	private oauthService: OAuthService;
 	private supabaseClient: SupabaseAuthClient;
 	private organizationService?: OrganizationService;
+	private logger = getLogger('AuthManager');
+	private refreshPromise: Promise<AuthCredentials> | null = null;
 
 	private constructor(config?: Partial<AuthConfig>) {
 		this.credentialStore = CredentialStore.getInstance(config);
@@ -36,7 +38,10 @@ export class AuthManager {
 		this.oauthService = new OAuthService(this.credentialStore, config);
 
 		// Initialize Supabase client with session restoration
-		this.initializeSupabaseSession();
+		// Fire-and-forget with catch handler to prevent unhandled rejections
+		this.initializeSupabaseSession().catch(() => {
+			// Errors are already logged in initializeSupabaseSession
+		});
 	}
 
 	/**
@@ -78,8 +83,60 @@ export class AuthManager {
 
 	/**
 	 * Get stored authentication credentials
+	 * Automatically refreshes the token if expired
 	 */
-	getCredentials(): AuthCredentials | null {
+	async getCredentials(): Promise<AuthCredentials | null> {
+		const credentials = this.credentialStore.getCredentials({
+			allowExpired: true
+		});
+
+		if (!credentials) {
+			return null;
+		}
+
+		// Check if credentials are expired (with 30-second clock skew buffer)
+		const CLOCK_SKEW_MS = 30_000;
+		const isExpired = credentials.expiresAt
+			? new Date(credentials.expiresAt).getTime() <= Date.now() + CLOCK_SKEW_MS
+			: false;
+
+		// If expired and we have a refresh token, attempt refresh
+		if (isExpired && credentials.refreshToken) {
+			// Return existing refresh promise if one is in progress
+			if (this.refreshPromise) {
+				try {
+					return await this.refreshPromise;
+				} catch {
+					return null;
+				}
+			}
+
+			try {
+				this.logger.info('Token expired, attempting automatic refresh...');
+				this.refreshPromise = this.refreshToken();
+				const result = await this.refreshPromise;
+				return result;
+			} catch (error) {
+				this.logger.warn('Automatic token refresh failed:', error);
+				return null;
+			} finally {
+				this.refreshPromise = null;
+			}
+		}
+
+		// Return null if expired and no refresh token
+		if (isExpired) {
+			return null;
+		}
+
+		return credentials;
+	}
+
+	/**
+	 * Get stored authentication credentials (synchronous version)
+	 * Does not attempt automatic refresh
+	 */
+	getCredentialsSync(): AuthCredentials | null {
 		return this.credentialStore.getCredentials();
 	}
 
@@ -171,8 +228,8 @@ export class AuthManager {
 	/**
 	 * Get the current user context (org/brief selection)
 	 */
-	getContext(): UserContext | null {
-		const credentials = this.getCredentials();
+	async getContext(): Promise<UserContext | null> {
+		const credentials = await this.getCredentials();
 		return credentials?.selectedContext || null;
 	}
 
@@ -180,7 +237,7 @@ export class AuthManager {
 	 * Update the user context (org/brief selection)
 	 */
 	async updateContext(context: Partial<UserContext>): Promise<void> {
-		const credentials = this.getCredentials();
+		const credentials = await this.getCredentials();
 		if (!credentials) {
 			throw new AuthenticationError('Not authenticated', 'NOT_AUTHENTICATED');
 		}
@@ -206,7 +263,7 @@ export class AuthManager {
 	 * Clear the user context
 	 */
 	async clearContext(): Promise<void> {
-		const credentials = this.getCredentials();
+		const credentials = await this.getCredentials();
 		if (!credentials) {
 			throw new AuthenticationError('Not authenticated', 'NOT_AUTHENTICATED');
 		}
@@ -223,7 +280,7 @@ export class AuthManager {
 	private async getOrganizationService(): Promise<OrganizationService> {
 		if (!this.organizationService) {
 			// First check if we have credentials with a token
-			const credentials = this.getCredentials();
+			const credentials = await this.getCredentials();
 			if (!credentials || !credentials.token) {
 				throw new AuthenticationError('Not authenticated', 'NOT_AUTHENTICATED');
 			}

packages/tm-core/src/auth/credential-store.spec.ts

@@ -0,0 +1,289 @@
+/**
+ * @fileoverview Unit tests for CredentialStore token expiration handling
+ */
+
+import { afterEach, beforeEach, describe, expect, it } from 'vitest';
+import fs from 'fs';
+import path from 'path';
+import os from 'os';
+import { CredentialStore } from './credential-store';
+import type { AuthCredentials } from './types';
+
+describe('CredentialStore - Token Expiration', () => {
+	let credentialStore: CredentialStore;
+	let tmpDir: string;
+	let authFile: string;
+
+	beforeEach(() => {
+		// Create temp directory for test credentials
+		tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'tm-cred-test-'));
+		authFile = path.join(tmpDir, 'auth.json');
+
+		// Create instance with test config
+		CredentialStore.resetInstance();
+		credentialStore = CredentialStore.getInstance({
+			configDir: tmpDir,
+			configFile: authFile
+		});
+	});
+
+	afterEach(() => {
+		// Clean up
+		try {
+			if (fs.existsSync(tmpDir)) {
+				fs.rmSync(tmpDir, { recursive: true, force: true });
+			}
+		} catch {
+			// Ignore cleanup errors
+		}
+		CredentialStore.resetInstance();
+	});
+
+	describe('Expiration Detection', () => {
+		it('should return null for expired token', () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(), // 1 minute ago
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).toBeNull();
+		});
+
+		it('should return credentials for valid token', () => {
+			const validCredentials: AuthCredentials = {
+				token: 'valid-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 3600000).toISOString(), // 1 hour from now
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(validCredentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).not.toBeNull();
+			expect(retrieved?.token).toBe('valid-token');
+		});
+
+		it('should return expired token when allowExpired is true', () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			const retrieved = credentialStore.getCredentials({ allowExpired: true });
+
+			expect(retrieved).not.toBeNull();
+			expect(retrieved?.token).toBe('expired-token');
+		});
+	});
+
+	describe('Clock Skew Tolerance', () => {
+		it('should reject token expiring within 30-second buffer', () => {
+			// Token expires in 15 seconds (within 30-second buffer)
+			const almostExpiredCredentials: AuthCredentials = {
+				token: 'almost-expired-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 15000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(almostExpiredCredentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).toBeNull();
+		});
+
+		it('should accept token expiring outside 30-second buffer', () => {
+			// Token expires in 60 seconds (outside 30-second buffer)
+			const validCredentials: AuthCredentials = {
+				token: 'valid-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(validCredentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).not.toBeNull();
+			expect(retrieved?.token).toBe('valid-token');
+		});
+	});
+
+	describe('Timestamp Format Handling', () => {
+		it('should handle ISO string timestamps', () => {
+			const credentials: AuthCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 3600000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(credentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).not.toBeNull();
+			expect(typeof retrieved?.expiresAt).toBe('number'); // Normalized to number
+		});
+
+		it('should handle numeric timestamps', () => {
+			const credentials: AuthCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: Date.now() + 3600000,
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(credentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).not.toBeNull();
+			expect(typeof retrieved?.expiresAt).toBe('number');
+		});
+
+		it('should return null for invalid timestamp format', () => {
+			// Manually write invalid timestamp to file
+			const invalidCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: 'invalid-date',
+				savedAt: new Date().toISOString()
+			};
+
+			fs.writeFileSync(authFile, JSON.stringify(invalidCredentials), {
+				mode: 0o600
+			});
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).toBeNull();
+		});
+
+		it('should return null for missing expiresAt', () => {
+			const credentialsWithoutExpiry = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				savedAt: new Date().toISOString()
+			};
+
+			fs.writeFileSync(authFile, JSON.stringify(credentialsWithoutExpiry), {
+				mode: 0o600
+			});
+
+			const retrieved = credentialStore.getCredentials();
+
+			expect(retrieved).toBeNull();
+		});
+	});
+
+	describe('Storage Persistence', () => {
+		it('should persist expiresAt as ISO string', () => {
+			const expiryTime = Date.now() + 3600000;
+			const credentials: AuthCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: expiryTime,
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(credentials);
+
+			// Read raw file to verify format
+			const fileContent = fs.readFileSync(authFile, 'utf-8');
+			const parsed = JSON.parse(fileContent);
+
+			// Should be stored as ISO string
+			expect(typeof parsed.expiresAt).toBe('string');
+			expect(parsed.expiresAt).toMatch(/^\d{4}-\d{2}-\d{2}T/); // ISO format
+		});
+
+		it('should normalize timestamp on retrieval', () => {
+			const credentials: AuthCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 3600000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(credentials);
+
+			const retrieved = credentialStore.getCredentials();
+
+			// Should be normalized to number for runtime use
+			expect(typeof retrieved?.expiresAt).toBe('number');
+		});
+	});
+
+	describe('hasValidCredentials', () => {
+		it('should return false for expired credentials', () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			expect(credentialStore.hasValidCredentials()).toBe(false);
+		});
+
+		it('should return true for valid credentials', () => {
+			const validCredentials: AuthCredentials = {
+				token: 'valid-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 3600000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(validCredentials);
+
+			expect(credentialStore.hasValidCredentials()).toBe(true);
+		});
+
+		it('should return false when no credentials exist', () => {
+			expect(credentialStore.hasValidCredentials()).toBe(false);
+		});
+	});
+});

packages/tm-core/src/repositories/supabase/supabase-task-repository.ts

@@ -47,8 +47,8 @@ export class SupabaseTaskRepository {
 	 * Gets the current brief ID from auth context
 	 * @throws {Error} If no brief is selected
 	 */
-	private getBriefIdOrThrow(): string {
-		const context = this.authManager.getContext();
+	private async getBriefIdOrThrow(): Promise<string> {
+		const context = await this.authManager.getContext();
 		if (!context?.briefId) {
 			throw new Error(
 				'No brief selected. Please select a brief first using: tm context brief'
@@ -61,7 +61,7 @@ export class SupabaseTaskRepository {
 		_projectId?: string,
 		options?: LoadTasksOptions
 	): Promise<Task[]> {
-		const briefId = this.getBriefIdOrThrow();
+		const briefId = await this.getBriefIdOrThrow();
 
 		// Build query with filters
 		let query = this.supabase
@@ -114,7 +114,7 @@ export class SupabaseTaskRepository {
 	}
 
 	async getTask(_projectId: string, taskId: string): Promise<Task | null> {
-		const briefId = this.getBriefIdOrThrow();
+		const briefId = await this.getBriefIdOrThrow();
 
 		const { data, error } = await this.supabase
 			.from('tasks')
@@ -157,7 +157,7 @@ export class SupabaseTaskRepository {
 		taskId: string,
 		updates: Partial<Task>
 	): Promise<Task> {
-		const briefId = this.getBriefIdOrThrow();
+		const briefId = await this.getBriefIdOrThrow();
 
 		// Validate updates using Zod schema
 		try {

packages/tm-core/src/services/export.service.ts

@@ -105,7 +105,7 @@ export class ExportService {
 		}
 
 		// Get current context
-		const context = this.authManager.getContext();
+		const context = await this.authManager.getContext();
 
 		// Determine org and brief IDs
 		let orgId = options.orgId || context?.orgId;
@@ -232,7 +232,7 @@ export class ExportService {
 		hasBrief: boolean;
 		context: UserContext | null;
 	}> {
-		const context = this.authManager.getContext();
+		const context = await this.authManager.getContext();
 
 		return {
 			hasOrg: !!context?.orgId,
@@ -379,7 +379,7 @@ export class ExportService {
 			};
 
 			// Get auth token
-			const credentials = this.authManager.getCredentials();
+			const credentials = await this.authManager.getCredentials();
 			if (!credentials || !credentials.token) {
 				throw new Error('Not authenticated');
 			}

packages/tm-core/src/storage/api-storage.ts

@@ -119,7 +119,7 @@ export class ApiStorage implements IStorage {
 	private async loadTagsIntoCache(): Promise<void> {
 		try {
 			const authManager = AuthManager.getInstance();
-			const context = authManager.getContext();
+			const context = await authManager.getContext();
 
 			// If we have a selected brief, create a virtual "tag" for it
 			if (context?.briefId) {
@@ -152,7 +152,7 @@ export class ApiStorage implements IStorage {
 
 		try {
 			const authManager = AuthManager.getInstance();
-			const context = authManager.getContext();
+			const context = await authManager.getContext();
 
 			// If no brief is selected in context, throw an error
 			if (!context?.briefId) {
@@ -318,7 +318,7 @@ export class ApiStorage implements IStorage {
 
 		try {
 			const authManager = AuthManager.getInstance();
-			const context = authManager.getContext();
+			const context = await authManager.getContext();
 
 			// In our API-based system, we only have one "tag" at a time - the current brief
 			if (context?.briefId) {

packages/tm-core/src/storage/storage-factory.ts

@@ -72,8 +72,8 @@ export class StorageFactory {
 							{ storageType: 'api', missing }
 						);
 					}
-					// Use auth token from AuthManager
-					const credentials = authManager.getCredentials();
+					// Use auth token from AuthManager (synchronous - no auto-refresh here)
+					const credentials = authManager.getCredentialsSync();
 					if (credentials) {
 						// Merge with existing storage config, ensuring required fields
 						const nextStorage: StorageSettings = {
@@ -103,7 +103,7 @@ export class StorageFactory {
 
 				// Then check if authenticated via AuthManager
 				if (authManager.isAuthenticated()) {
-					const credentials = authManager.getCredentials();
+					const credentials = authManager.getCredentialsSync();
 					if (credentials) {
 						// Configure API storage with auth credentials
 						const nextStorage: StorageSettings = {

packages/tm-core/tests/auth/auth-refresh.test.ts

@@ -0,0 +1,176 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+import type { Session } from '@supabase/supabase-js';
+import { AuthManager } from '../../src/auth/auth-manager';
+import { CredentialStore } from '../../src/auth/credential-store';
+import type { AuthCredentials } from '../../src/auth/types';
+
+describe('AuthManager Token Refresh', () => {
+	let authManager: AuthManager;
+	let credentialStore: CredentialStore;
+	let tmpDir: string;
+	let authFile: string;
+
+	beforeEach(() => {
+		// Reset singletons
+		AuthManager.resetInstance();
+		CredentialStore.resetInstance();
+
+		// Create temporary directory for test isolation
+		tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'tm-auth-refresh-'));
+		authFile = path.join(tmpDir, 'auth.json');
+
+		// Initialize AuthManager with test config (this will create CredentialStore internally)
+		authManager = AuthManager.getInstance({
+			configDir: tmpDir,
+			configFile: authFile
+		});
+
+		// Get the CredentialStore instance that AuthManager created
+		credentialStore = CredentialStore.getInstance();
+		credentialStore.clearCredentials();
+	});
+
+	afterEach(() => {
+		// Clean up
+		try {
+			credentialStore.clearCredentials();
+		} catch {
+			// Ignore cleanup errors
+		}
+		AuthManager.resetInstance();
+		CredentialStore.resetInstance();
+		vi.restoreAllMocks();
+
+		// Remove temporary directory
+		if (tmpDir && fs.existsSync(tmpDir)) {
+			fs.rmSync(tmpDir, { recursive: true, force: true });
+		}
+	});
+
+	it('should not make concurrent refresh requests', async () => {
+		// Set up expired credentials with refresh token
+		const expiredCredentials: AuthCredentials = {
+			token: 'expired_access_token',
+			refreshToken: 'valid_refresh_token',
+			userId: 'test-user-id',
+			email: 'test@example.com',
+			expiresAt: new Date(Date.now() - 1000).toISOString(), // Expired 1 second ago
+			savedAt: new Date().toISOString()
+		};
+
+		credentialStore.saveCredentials(expiredCredentials);
+
+		// Mock the refreshToken method to track calls
+		const refreshTokenSpy = vi.spyOn(authManager as any, 'refreshToken');
+		const mockSession: Session = {
+			access_token: 'new_access_token',
+			refresh_token: 'new_refresh_token',
+			expires_at: Math.floor(Date.now() / 1000) + 3600,
+			user: {
+				id: 'test-user-id',
+				email: 'test@example.com',
+				app_metadata: {},
+				user_metadata: {},
+				aud: 'authenticated',
+				created_at: new Date().toISOString()
+			}
+		};
+
+		refreshTokenSpy.mockResolvedValue({
+			token: mockSession.access_token,
+			refreshToken: mockSession.refresh_token,
+			userId: mockSession.user.id,
+			email: mockSession.user.email,
+			expiresAt: new Date(mockSession.expires_at! * 1000).toISOString(),
+			savedAt: new Date().toISOString()
+		});
+
+		// Make multiple concurrent calls to getCredentials
+		const promises = [
+			authManager.getCredentials(),
+			authManager.getCredentials(),
+			authManager.getCredentials()
+		];
+
+		const results = await Promise.all(promises);
+
+		// Verify all calls returned the same new credentials
+		expect(results[0]?.token).toBe('new_access_token');
+		expect(results[1]?.token).toBe('new_access_token');
+		expect(results[2]?.token).toBe('new_access_token');
+
+		// Verify refreshToken was only called once, not three times
+		expect(refreshTokenSpy).toHaveBeenCalledTimes(1);
+	});
+
+	it('should return valid credentials without attempting refresh', async () => {
+		// Set up valid (non-expired) credentials
+		const validCredentials: AuthCredentials = {
+			token: 'valid_access_token',
+			refreshToken: 'valid_refresh_token',
+			userId: 'test-user-id',
+			email: 'test@example.com',
+			expiresAt: new Date(Date.now() + 3600000).toISOString(), // Expires in 1 hour
+			savedAt: new Date().toISOString()
+		};
+
+		credentialStore.saveCredentials(validCredentials);
+
+		// Spy on refreshToken to ensure it's not called
+		const refreshTokenSpy = vi.spyOn(authManager as any, 'refreshToken');
+
+		const credentials = await authManager.getCredentials();
+
+		expect(credentials?.token).toBe('valid_access_token');
+		expect(refreshTokenSpy).not.toHaveBeenCalled();
+	});
+
+	it('should return null if credentials are expired with no refresh token', async () => {
+		// Set up expired credentials WITHOUT refresh token
+		const expiredCredentials: AuthCredentials = {
+			token: 'expired_access_token',
+			refreshToken: undefined,
+			userId: 'test-user-id',
+			email: 'test@example.com',
+			expiresAt: new Date(Date.now() - 1000).toISOString(), // Expired 1 second ago
+			savedAt: new Date().toISOString()
+		};
+
+		credentialStore.saveCredentials(expiredCredentials);
+
+		const credentials = await authManager.getCredentials();
+
+		expect(credentials).toBeNull();
+	});
+
+	it('should return null if no credentials exist', async () => {
+		const credentials = await authManager.getCredentials();
+		expect(credentials).toBeNull();
+	});
+
+	it('should handle refresh failures gracefully', async () => {
+		// Set up expired credentials with refresh token
+		const expiredCredentials: AuthCredentials = {
+			token: 'expired_access_token',
+			refreshToken: 'invalid_refresh_token',
+			userId: 'test-user-id',
+			email: 'test@example.com',
+			expiresAt: new Date(Date.now() - 1000).toISOString(),
+			savedAt: new Date().toISOString()
+		};
+
+		credentialStore.saveCredentials(expiredCredentials);
+
+		// Mock refreshToken to throw an error
+		const refreshTokenSpy = vi.spyOn(authManager as any, 'refreshToken');
+		refreshTokenSpy.mockRejectedValue(new Error('Refresh failed'));
+
+		const credentials = await authManager.getCredentials();
+
+		expect(credentials).toBeNull();
+		expect(refreshTokenSpy).toHaveBeenCalledTimes(1);
+	});
+});

packages/tm-core/tests/integration/auth-token-refresh.test.ts

@@ -0,0 +1,392 @@
+/**
+ * @fileoverview Integration tests for JWT token auto-refresh functionality
+ *
+ * These tests verify that expired tokens are automatically refreshed
+ * when making API calls through AuthManager.
+ */
+
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+import type { Session } from '@supabase/supabase-js';
+import { AuthManager } from '../../src/auth/auth-manager';
+import { CredentialStore } from '../../src/auth/credential-store';
+import type { AuthCredentials } from '../../src/auth/types';
+
+describe('AuthManager - Token Auto-Refresh Integration', () => {
+	let authManager: AuthManager;
+	let credentialStore: CredentialStore;
+	let tmpDir: string;
+	let authFile: string;
+
+	// Mock Supabase session that will be returned on refresh
+	const mockRefreshedSession: Session = {
+		access_token: 'new-access-token-xyz',
+		refresh_token: 'new-refresh-token-xyz',
+		token_type: 'bearer',
+		expires_at: Math.floor(Date.now() / 1000) + 3600, // 1 hour from now
+		expires_in: 3600,
+		user: {
+			id: 'test-user-id',
+			email: 'test@example.com',
+			aud: 'authenticated',
+			role: 'authenticated',
+			app_metadata: {},
+			user_metadata: {},
+			created_at: new Date().toISOString()
+		}
+	};
+
+	beforeEach(() => {
+		// Reset singletons
+		AuthManager.resetInstance();
+		CredentialStore.resetInstance();
+
+		// Create temporary directory for test isolation
+		tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'tm-auth-integration-'));
+		authFile = path.join(tmpDir, 'auth.json');
+
+		// Initialize AuthManager with test config (this will create CredentialStore internally)
+		authManager = AuthManager.getInstance({
+			configDir: tmpDir,
+			configFile: authFile
+		});
+
+		// Get the CredentialStore instance that AuthManager created
+		credentialStore = CredentialStore.getInstance();
+		credentialStore.clearCredentials();
+	});
+
+	afterEach(() => {
+		// Clean up
+		try {
+			credentialStore.clearCredentials();
+		} catch {
+			// Ignore cleanup errors
+		}
+		AuthManager.resetInstance();
+		CredentialStore.resetInstance();
+		vi.restoreAllMocks();
+
+		// Remove temporary directory
+		if (tmpDir && fs.existsSync(tmpDir)) {
+			fs.rmSync(tmpDir, { recursive: true, force: true });
+		}
+	});
+
+	describe('Expired Token Detection', () => {
+		it('should detect expired token', async () => {
+			// Set up expired credentials
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(), // 1 minute ago
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			// Mock the Supabase refreshSession to return new tokens
+			const mockRefreshSession = vi
+				.fn()
+				.mockResolvedValue(mockRefreshedSession);
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockImplementation(mockRefreshSession);
+
+			// Get credentials should trigger refresh
+			const credentials = await authManager.getCredentials();
+
+			expect(mockRefreshSession).toHaveBeenCalledTimes(1);
+			expect(credentials).not.toBeNull();
+			expect(credentials?.token).toBe('new-access-token-xyz');
+		});
+
+		it('should not refresh valid token', async () => {
+			// Set up valid credentials
+			const validCredentials: AuthCredentials = {
+				token: 'valid-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 3600000).toISOString(), // 1 hour from now
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(validCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			// Mock refresh to ensure it's not called
+			const mockRefreshSession = vi.fn();
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockImplementation(mockRefreshSession);
+
+			const credentials = await authManager.getCredentials();
+
+			expect(mockRefreshSession).not.toHaveBeenCalled();
+			expect(credentials?.token).toBe('valid-token');
+		});
+	});
+
+	describe('Token Refresh Flow', () => {
+		it('should refresh expired token and save new credentials', async () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'old-token',
+				refreshToken: 'old-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date(Date.now() - 3600000).toISOString(),
+				selectedContext: {
+					orgId: 'test-org',
+					briefId: 'test-brief',
+					updatedAt: new Date().toISOString()
+				}
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockResolvedValue(mockRefreshedSession);
+
+			const refreshedCredentials = await authManager.getCredentials();
+
+			expect(refreshedCredentials).not.toBeNull();
+			expect(refreshedCredentials?.token).toBe('new-access-token-xyz');
+			expect(refreshedCredentials?.refreshToken).toBe('new-refresh-token-xyz');
+
+			// Verify context was preserved
+			expect(refreshedCredentials?.selectedContext?.orgId).toBe('test-org');
+			expect(refreshedCredentials?.selectedContext?.briefId).toBe('test-brief');
+
+			// Verify new expiration is in the future
+			const newExpiry = new Date(refreshedCredentials!.expiresAt!).getTime();
+			const now = Date.now();
+			expect(newExpiry).toBeGreaterThan(now);
+		});
+
+		it('should return null if refresh fails', async () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'invalid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			// Mock refresh to fail
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockRejectedValue(new Error('Refresh token expired'));
+
+			const credentials = await authManager.getCredentials();
+
+			expect(credentials).toBeNull();
+		});
+
+		it('should return null if no refresh token available', async () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				// No refresh token
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			const credentials = await authManager.getCredentials();
+
+			expect(credentials).toBeNull();
+		});
+
+		it('should return null if credentials missing expiresAt', async () => {
+			const credentialsWithoutExpiry: AuthCredentials = {
+				token: 'test-token',
+				refreshToken: 'refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				// Missing expiresAt
+				savedAt: new Date().toISOString()
+			} as any;
+
+			credentialStore.saveCredentials(credentialsWithoutExpiry);
+
+			authManager = AuthManager.getInstance();
+
+			const credentials = await authManager.getCredentials();
+
+			// Should return null because no valid expiration
+			expect(credentials).toBeNull();
+		});
+	});
+
+	describe('Clock Skew Tolerance', () => {
+		it('should refresh token within 30-second expiry window', async () => {
+			// Token expires in 15 seconds (within 30-second buffer)
+			const almostExpiredCredentials: AuthCredentials = {
+				token: 'almost-expired-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 15000).toISOString(), // 15 seconds from now
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(almostExpiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			const mockRefreshSession = vi
+				.fn()
+				.mockResolvedValue(mockRefreshedSession);
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockImplementation(mockRefreshSession);
+
+			const credentials = await authManager.getCredentials();
+
+			// Should trigger refresh due to 30-second buffer
+			expect(mockRefreshSession).toHaveBeenCalledTimes(1);
+			expect(credentials?.token).toBe('new-access-token-xyz');
+		});
+
+		it('should not refresh token well before expiry', async () => {
+			// Token expires in 5 minutes (well outside 30-second buffer)
+			const validCredentials: AuthCredentials = {
+				token: 'valid-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() + 300000).toISOString(), // 5 minutes
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(validCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			const mockRefreshSession = vi.fn();
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockImplementation(mockRefreshSession);
+
+			const credentials = await authManager.getCredentials();
+
+			expect(mockRefreshSession).not.toHaveBeenCalled();
+			expect(credentials?.token).toBe('valid-token');
+		});
+	});
+
+	describe('Synchronous vs Async Methods', () => {
+		it('getCredentialsSync should not trigger refresh', () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			// Synchronous call should return null without refresh
+			const credentials = authManager.getCredentialsSync();
+
+			expect(credentials).toBeNull();
+		});
+
+		it('getCredentials async should trigger refresh', async () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockResolvedValue(mockRefreshedSession);
+
+			const credentials = await authManager.getCredentials();
+
+			expect(credentials).not.toBeNull();
+			expect(credentials?.token).toBe('new-access-token-xyz');
+		});
+	});
+
+	describe('Multiple Concurrent Calls', () => {
+		it('should handle concurrent getCredentials calls gracefully', async () => {
+			const expiredCredentials: AuthCredentials = {
+				token: 'expired-token',
+				refreshToken: 'valid-refresh-token',
+				userId: 'test-user-id',
+				email: 'test@example.com',
+				expiresAt: new Date(Date.now() - 60000).toISOString(),
+				savedAt: new Date().toISOString()
+			};
+
+			credentialStore.saveCredentials(expiredCredentials);
+
+			authManager = AuthManager.getInstance();
+
+			const mockRefreshSession = vi
+				.fn()
+				.mockResolvedValue(mockRefreshedSession);
+			vi.spyOn(
+				authManager['supabaseClient'],
+				'refreshSession'
+			).mockImplementation(mockRefreshSession);
+
+			// Make multiple concurrent calls
+			const [creds1, creds2, creds3] = await Promise.all([
+				authManager.getCredentials(),
+				authManager.getCredentials(),
+				authManager.getCredentials()
+			]);
+
+			// All should get the refreshed token
+			expect(creds1?.token).toBe('new-access-token-xyz');
+			expect(creds2?.token).toBe('new-access-token-xyz');
+			expect(creds3?.token).toBe('new-access-token-xyz');
+
+			// Refresh might be called multiple times, but that's okay
+			// (ideally we'd debounce, but this is acceptable behavior)
+			expect(mockRefreshSession).toHaveBeenCalled();
+		});
+	});
+});