diff --git a/src/core/AuthKitCore.ts b/src/core/AuthKitCore.ts
index 181798c..dfbbb11 100644
--- a/src/core/AuthKitCore.ts
+++ b/src/core/AuthKitCore.ts
@@ -152,12 +152,14 @@ export class AuthKitCore {
    *
    * @param refreshToken - The refresh token
    * @param organizationId - Optional organization ID to switch to
+   * @param context - Optional context for error reporting (userId, sessionId)
    * @returns New access token, refresh token, user, and impersonator
    * @throws TokenRefreshError if refresh fails
    */
   async refreshTokens(
     refreshToken: string,
     organizationId?: string,
+    context?: { userId?: string; sessionId?: string },
   ): Promise<{
     accessToken: string;
     refreshToken: string;
@@ -179,7 +181,7 @@ export class AuthKitCore {
         impersonator: result.impersonator,
       };
     } catch (error) {
-      throw new TokenRefreshError('Failed to refresh tokens', error);
+      throw new TokenRefreshError('Failed to refresh tokens', error, context);
     }
   }
 
@@ -226,9 +228,18 @@ export class AuthKitCore {
       }
     }
 
+    // Extract session ID for error context (works on expired tokens too)
+    let sessionId: string | undefined;
+    try {
+      sessionId = this.parseTokenClaims(accessToken).sid;
+    } catch {
+      // Token parsing failed - continue without session context
+    }
+
     const newSession = await this.refreshTokens(
       session.refreshToken,
       organizationId,
+      { userId: session.user?.id, sessionId },
     );
     const newClaims = this.parseTokenClaims<TCustomClaims>(
       newSession.accessToken,
diff --git a/src/core/errors.spec.ts b/src/core/errors.spec.ts
index 8561a0e..c75d959 100644
--- a/src/core/errors.spec.ts
+++ b/src/core/errors.spec.ts
@@ -93,6 +93,53 @@ describe('TokenRefreshError', () => {
 
     expect(error.cause).toBe(originalError);
   });
+
+  it('creates error with userId and sessionId', () => {
+    const error = new TokenRefreshError('Refresh failed', undefined, {
+      userId: 'user_123',
+      sessionId: 'session_456',
+    });
+
+    expect(error.userId).toBe('user_123');
+    expect(error.sessionId).toBe('session_456');
+  });
+
+  it('creates error with cause and context', () => {
+    const originalError = new Error('Network error');
+    const error = new TokenRefreshError('Refresh failed', originalError, {
+      userId: 'user_123',
+      sessionId: 'session_456',
+    });
+
+    expect(error.cause).toBe(originalError);
+    expect(error.userId).toBe('user_123');
+    expect(error.sessionId).toBe('session_456');
+  });
+
+  it('creates error with partial context (userId only)', () => {
+    const error = new TokenRefreshError('Refresh failed', undefined, {
+      userId: 'user_123',
+    });
+
+    expect(error.userId).toBe('user_123');
+    expect(error.sessionId).toBeUndefined();
+  });
+
+  it('creates error with partial context (sessionId only)', () => {
+    const error = new TokenRefreshError('Refresh failed', undefined, {
+      sessionId: 'session_456',
+    });
+
+    expect(error.userId).toBeUndefined();
+    expect(error.sessionId).toBe('session_456');
+  });
+
+  it('has undefined properties when no context provided', () => {
+    const error = new TokenRefreshError('Refresh failed');
+
+    expect(error.userId).toBeUndefined();
+    expect(error.sessionId).toBeUndefined();
+  });
 });
 
 describe('error inheritance', () => {
diff --git a/src/core/errors.ts b/src/core/errors.ts
index cdb9bf3..313c62c 100644
--- a/src/core/errors.ts
+++ b/src/core/errors.ts
@@ -24,8 +24,17 @@ export class TokenValidationError extends AuthKitError {
 }
 
 export class TokenRefreshError extends AuthKitError {
-  constructor(message: string, cause?: unknown) {
+  readonly userId?: string;
+  readonly sessionId?: string;
+
+  constructor(
+    message: string,
+    cause?: unknown,
+    context?: { userId?: string; sessionId?: string },
+  ) {
     super(message, cause);
     this.name = 'TokenRefreshError';
+    this.userId = context?.userId;
+    this.sessionId = context?.sessionId;
   }
 }
diff --git a/src/index.ts b/src/index.ts
index bded98d..511c63d 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -58,6 +58,16 @@ export { ConfigurationProvider } from './core/config/ConfigurationProvider.js';
 // ============================================
 export { getWorkOS } from './core/client/workos.js';
 
+// ============================================
+// Errors
+// ============================================
+export {
+  AuthKitError,
+  SessionEncryptionError,
+  TokenValidationError,
+  TokenRefreshError,
+} from './core/errors.js';
+
 // ============================================
 // Type Exports
 // ============================================