diff --git a/web/cypress/e2e/signin.cy.ts b/web/cypress/e2e/signin.cy.ts
index 93cb09833..1c5075d10 100644
--- a/web/cypress/e2e/signin.cy.ts
+++ b/web/cypress/e2e/signin.cy.ts
@@ -234,6 +234,78 @@ describe('Signin page', () => {
     // Should not redirect
     cy.url().should('include', '/signin');
   });
+
+  it('Redirects to username confirmation page when user has prompts', () => {
+    // Mock successful login
+    setupSuccessfulSignin();
+
+    // Mock user API to return user with confirm_username prompt
+    cy.intercept('GET', '/api/v1/user/', {
+      statusCode: 200,
+      body: {
+        anonymous: false,
+        username: 'test_ldap_user',
+        email: 'test@example.com',
+        verified: true,
+        prompts: ['confirm_username'],
+        organizations: [],
+        logins: [
+          {
+            service: 'ldap',
+            service_identifier: 'test_ldap_user',
+            metadata: {
+              service_username: 'test_ldap_user',
+            },
+          },
+        ],
+      },
+    }).as('getUserWithPrompt');
+
+    // Fill and submit login form
+    cy.get('#pf-login-username-id').type('test_ldap_user');
+    cy.get('#pf-login-password-id').type('password');
+    cy.get('button[type=submit]').click();
+
+    // Wait for signin and user fetch
+    cy.wait('@signinSuccess');
+    cy.wait('@getCsrfToken');
+    cy.wait('@getUserWithPrompt');
+
+    // Should redirect to updateuser page for username confirmation
+    cy.url().should('include', '/updateuser');
+  });
+
+  it('Redirects to organization page when user has no prompts', () => {
+    // Mock successful login
+    setupSuccessfulSignin();
+
+    // Mock user API to return user without prompts
+    cy.intercept('GET', '/api/v1/user/', {
+      statusCode: 200,
+      body: {
+        anonymous: false,
+        username: 'user1',
+        email: 'user1@example.com',
+        verified: true,
+        prompts: [],
+        organizations: [],
+        logins: [],
+      },
+    }).as('getUserNoPrompt');
+
+    // Fill and submit login form
+    cy.get('#pf-login-username-id').type('user1');
+    cy.get('#pf-login-password-id').type('password');
+    cy.get('button[type=submit]').click();
+
+    // Wait for signin and user fetch
+    cy.wait('@signinSuccess');
+    cy.wait('@getCsrfToken');
+    cy.wait('@getUserNoPrompt');
+
+    // Should redirect to organization page
+    cy.url().should('include', '/organization');
+  });
 });
 
 describe('Forgot Password functionality', () => {
diff --git a/web/src/routes/Signin/Signin.tsx b/web/src/routes/Signin/Signin.tsx
index abecad36a..26137f16f 100644
--- a/web/src/routes/Signin/Signin.tsx
+++ b/web/src/routes/Signin/Signin.tsx
@@ -26,6 +26,8 @@ import {useExternalLogins} from 'src/hooks/UseExternalLogins';
 import {useExternalLoginAuth} from 'src/hooks/UseExternalLoginAuth';
 import {ExternalLoginButton} from 'src/components/ExternalLoginButton';
 import {LoginPageLayout} from 'src/components/LoginPageLayout';
+import {useQueryClient} from '@tanstack/react-query';
+import {fetchUser} from 'src/resources/UserResource';
 
 type ViewType = 'signin' | 'forgotPassword';
 
@@ -48,6 +50,7 @@ export function Signin() {
   const navigate = useNavigate();
   const quayConfig = useQuayConfig();
   const [searchParams] = useSearchParams();
+  const queryClient = useQueryClient();
   const {
     requestRecovery,
     isLoading: sendingRecovery,
@@ -170,6 +173,29 @@ export function Signin() {
         setAuthState((old) => ({...old, isSignedIn: true, username: username}));
         await getCsrfToken();
         GlobalAuthState.isLoggedIn = true;
+
+        // Fetch fresh user data to check for prompts
+        let user;
+        try {
+          user = await queryClient.fetchQuery(['user'], fetchUser);
+        } catch (fetchErr) {
+          // If fetching user fails, show error and stop navigation
+          setErr(
+            addDisplayError(
+              'Login successful but failed to load user data. Please refresh the page.',
+              fetchErr,
+            ),
+          );
+          return;
+        }
+
+        // If user has prompts (e.g., confirm_username), redirect to updateuser
+        if (user.prompts && user.prompts.length > 0) {
+          navigate('/updateuser');
+          return;
+        }
+
+        // Otherwise, redirect to the intended destination
         const redirectUrl = searchParams.get('redirect_url');
         if (redirectUrl) {
           window.location.href = redirectUrl;
diff --git a/web/src/routes/UpdateUser/UpdateUser.tsx b/web/src/routes/UpdateUser/UpdateUser.tsx
index 9b3616d6a..a5b6a0878 100644
--- a/web/src/routes/UpdateUser/UpdateUser.tsx
+++ b/web/src/routes/UpdateUser/UpdateUser.tsx
@@ -47,6 +47,38 @@ export default function UpdateUser() {
       if (updatedUser?.prompts?.length) {
         setIsUpdating(false);
       } else {
+        // Check for stored redirect URL (set by external login flow)
+        const redirectUrl = localStorage.getItem('quay.redirectAfterLoad');
+        localStorage.removeItem('quay.redirectAfterLoad');
+
+        if (redirectUrl) {
+          // Validate redirect URL to prevent open redirect vulnerability
+          try {
+            // Allow relative paths (starting with /)
+            if (redirectUrl.startsWith('/')) {
+              window.location.href = redirectUrl;
+              return;
+            }
+
+            // For absolute URLs, validate they are same-origin
+            const url = new URL(redirectUrl);
+            if (url.origin === window.location.origin) {
+              window.location.href = redirectUrl;
+              return;
+            }
+
+            // Invalid URL - fall through to default navigation
+            console.warn(
+              'Ignoring redirect URL from different origin:',
+              redirectUrl,
+            );
+          } catch (err) {
+            // Invalid URL format - fall through to default navigation
+            console.warn('Invalid redirect URL format:', redirectUrl, err);
+          }
+        }
+
+        // Default navigation if no valid redirect URL
         navigate('/');
       }
     },