diff --git a/src/server/auth-helpers.spec.ts b/src/server/auth-helpers.spec.ts
index 9c824f8..e7842f2 100644
--- a/src/server/auth-helpers.spec.ts
+++ b/src/server/auth-helpers.spec.ts
@@ -97,26 +97,24 @@ describe('Auth Helpers', () => {
       expect(result).toBeNull();
     });
 
-    it('returns null when no refresh token in session', async () => {
+    it('returns null when no refresh token in auth context', async () => {
       mockAuthContext = {
         auth: () => ({ user: { id: 'user_123' }, accessToken: 'token' }),
         request: new Request('http://test.local'),
       };
-      mockAuthkit.getSession.mockResolvedValue({ refreshToken: null });
 
       const result = await getSessionWithRefreshToken();
 
       expect(result).toBeNull();
     });
 
-    it('returns session data with refresh token', async () => {
+    it('returns session data with refresh token from auth context', async () => {
       const user = { id: 'user_123', email: 'test@example.com' };
       const impersonator = { email: 'admin@example.com' };
       mockAuthContext = {
-        auth: () => ({ user, accessToken: 'access_token', impersonator }),
+        auth: () => ({ user, accessToken: 'access_token', refreshToken: 'refresh_token', impersonator }),
         request: new Request('http://test.local'),
       };
-      mockAuthkit.getSession.mockResolvedValue({ refreshToken: 'refresh_token' });
 
       const result = await getSessionWithRefreshToken();
 
@@ -127,6 +125,37 @@ describe('Auth Helpers', () => {
         impersonator,
       });
     });
+
+    it('uses middleware-refreshed token instead of stale request token', async () => {
+      // Simulates the case where middleware auto-refreshed the session
+      // (e.g., expired access token). The auth context has the NEW refresh token,
+      // while the original request cookie has the OLD (invalidated) one.
+      const user = { id: 'user_123' };
+      mockAuthContext = {
+        auth: () => ({
+          user,
+          accessToken: 'new_access_token',
+          refreshToken: 'new_refresh_token', // refreshed by middleware
+          impersonator: undefined,
+        }),
+        request: new Request('http://test.local', {
+          headers: { cookie: 'wos-session=old_encrypted_session' },
+        }),
+      };
+
+      const result = await getSessionWithRefreshToken();
+
+      // Should use the NEW refresh token from auth context, not the old one from request
+      expect(result).toEqual({
+        refreshToken: 'new_refresh_token',
+        accessToken: 'new_access_token',
+        user,
+        impersonator: undefined,
+      });
+
+      // Should NOT call getSession on the request (no longer needed)
+      expect(mockAuthkit.getSession).not.toHaveBeenCalled();
+    });
   });
 
   describe('refreshSession', () => {
@@ -144,10 +173,9 @@ describe('Auth Helpers', () => {
     it('refreshes session and saves encrypted session', async () => {
       const user = { id: 'user_123' };
       mockAuthContext = {
-        auth: () => ({ user, accessToken: 'old_token' }),
+        auth: () => ({ user, accessToken: 'old_token', refreshToken: 'refresh_token' }),
         request: new Request('http://test.local'),
       };
-      mockAuthkit.getSession.mockResolvedValue({ refreshToken: 'refresh_token' });
       mockAuthkit.refreshSession.mockResolvedValue({
         auth: { user, accessToken: 'new_token', sessionId: 'session_123' },
         encryptedSession: 'encrypted_data',
@@ -171,10 +199,9 @@ describe('Auth Helpers', () => {
     it('does not save session when no encrypted data', async () => {
       const user = { id: 'user_123' };
       mockAuthContext = {
-        auth: () => ({ user, accessToken: 'token' }),
+        auth: () => ({ user, accessToken: 'token', refreshToken: 'refresh_token' }),
         request: new Request('http://test.local'),
       };
-      mockAuthkit.getSession.mockResolvedValue({ refreshToken: 'refresh_token' });
       mockAuthkit.refreshSession.mockResolvedValue({
         auth: { user },
         encryptedSession: null,
diff --git a/src/server/auth-helpers.ts b/src/server/auth-helpers.ts
index 22bd62c..3ecd4dc 100644
--- a/src/server/auth-helpers.ts
+++ b/src/server/auth-helpers.ts
@@ -28,7 +28,9 @@ export function getRedirectUriFromContext(): string | undefined {
 }
 
 /**
- * Gets the session with refresh token from the current request.
+ * Gets the session with refresh token from the auth context.
+ * Uses the middleware auth context which always has the latest refresh token,
+ * even if the middleware auto-refreshed during withAuth().
  * Returns null if no valid session exists.
  */
 export async function getSessionWithRefreshToken(): Promise<{
@@ -43,16 +45,17 @@ export async function getSessionWithRefreshToken(): Promise<{
     return null;
   }
 
-  const ctx = getAuthKitContext();
-  const authkit = await getAuthkit();
-  const session = await authkit.getSession(ctx.request);
-
-  if (!session?.refreshToken) {
+  // Use the refresh token from the auth context — it's always up-to-date.
+  // Previously we re-read the session from the original request, but if the
+  // middleware auto-refreshed (e.g., expired access token), the old refresh
+  // token in the request cookie would already be invalidated.
+  const refreshToken = 'refreshToken' in auth ? auth.refreshToken : undefined;
+  if (!refreshToken) {
     return null;
   }
 
   return {
-    refreshToken: session.refreshToken,
+    refreshToken,
     accessToken: auth.accessToken,
     user: auth.user,
     impersonator: auth.impersonator,