diff --git a/frontend/public/locales/en-GB/translation.json b/frontend/public/locales/en-GB/translation.json
index f9230a9534..62e9ce3f21 100644
--- a/frontend/public/locales/en-GB/translation.json
+++ b/frontend/public/locales/en-GB/translation.json
@@ -3229,6 +3229,12 @@
     "backendLoadingTitle": "Backend starting up",
     "backendLoadingMessage": "Backend is currently loading and/or not started. Please wait a few moments and try again."
   },
+  "backendStartup": {
+    "title": "Backend Starting",
+    "loadingTitle": "Backend starting up",
+    "loadingMessage": "The backend is currently starting up. This usually takes a few moments.",
+    "takingLonger": "This is taking longer than expected. The backend should be ready soon."
+  },
   "signup": {
     "title": "Create an account",
     "subtitle": "Join Stirling PDF to get started",
diff --git a/frontend/src/proprietary/App.tsx b/frontend/src/proprietary/App.tsx
index eba2fa5c4c..522f039ef9 100644
--- a/frontend/src/proprietary/App.tsx
+++ b/frontend/src/proprietary/App.tsx
@@ -7,6 +7,7 @@ import Login from "@app/routes/Login";
 import Signup from "@app/routes/Signup";
 import AuthCallback from "@app/routes/AuthCallback";
 import InviteAccept from "@app/routes/InviteAccept";
+import BackendStartup from "@app/routes/BackendStartup";
 import OnboardingTour from "@app/components/onboarding/OnboardingTour";
 
 // Import global styles
@@ -28,6 +29,7 @@ export default function App() {
           <Route path="/signup" element={<Signup />} />
           <Route path="/auth/callback" element={<AuthCallback />} />
           <Route path="/invite/:token" element={<InviteAccept />} />
+          <Route path="/backend-startup" element={<BackendStartup />} />
 
           {/* Main app routes - Landing handles auth logic */}
           <Route path="/*" element={<Landing />} />
diff --git a/frontend/src/proprietary/routes/BackendStartup.tsx b/frontend/src/proprietary/routes/BackendStartup.tsx
new file mode 100644
index 0000000000..a5bff3d37f
--- /dev/null
+++ b/frontend/src/proprietary/routes/BackendStartup.tsx
@@ -0,0 +1,183 @@
+import { useEffect, useState } from 'react';
+import { useNavigate } from 'react-router-dom';
+import { useTranslation } from 'react-i18next';
+import { useDocumentMeta } from '@app/hooks/useDocumentMeta';
+import AuthLayout from '@app/routes/authShared/AuthLayout';
+import { BASE_PATH } from '@app/constants/app';
+
+export default function BackendStartup() {
+  const navigate = useNavigate();
+  const { t } = useTranslation();
+  const [pollAttempt, setPollAttempt] = useState(0);
+  const [statusMessage, setStatusMessage] = useState<string | null>(null);
+  const baseUrl = window.location.origin + BASE_PATH;
+
+  // Set document meta
+  useDocumentMeta({
+    title: `${t('backendStartup.title', 'Backend Starting')} - Stirling PDF`,
+    description: t('app.description', 'The Free Adobe Acrobat alternative (10M+ Downloads)'),
+    ogTitle: `${t('backendStartup.title', 'Backend Starting')} - Stirling PDF`,
+    ogDescription: t('app.description', 'The Free Adobe Acrobat alternative (10M+ Downloads)'),
+    ogImage: `${baseUrl}/og_images/home.png`,
+    ogUrl: `${window.location.origin}${window.location.pathname}`
+  });
+
+  // Poll backend to check if it's ready
+  useEffect(() => {
+    let timeoutId: NodeJS.Timeout | null = null;
+    let isMounted = true;
+
+    const checkBackendStatus = async () => {
+      try {
+        // Use a universal endpoint that works in both proprietary and non-proprietary builds
+        // Try /api/v1/info/status first (works in both builds if metrics enabled)
+        const response = await fetch(`${BASE_PATH}/api/v1/info/status`, {
+          method: 'GET',
+          cache: 'no-cache'
+        });
+
+        if (!isMounted) return;
+
+        if (response.ok) {
+          const data = await response.json();
+
+          // Backend is ready if we get valid status back
+          if (data && data.status === 'UP') {
+            console.log('[BackendStartup] Backend is ready, redirecting');
+            const redirectTo = sessionStorage.getItem('backendStartupRedirect') || '/';
+            sessionStorage.removeItem('backendStartupRedirect');
+
+            // Small delay to ensure backend is fully ready
+            setTimeout(() => {
+              if (isMounted) {
+                navigate(redirectTo, { replace: true });
+              }
+            }, 500);
+            return;
+          }
+        }
+
+        // If status endpoint fails with 403 (metrics disabled), try proprietary endpoint
+        if (response.status === 403) {
+          console.debug('[BackendStartup] Metrics disabled, trying proprietary endpoint');
+          const proprietaryResponse = await fetch(`${BASE_PATH}/api/v1/proprietary/ui-data/login`, {
+            method: 'GET',
+            cache: 'no-cache'
+          });
+
+          if (!isMounted) return;
+
+          if (proprietaryResponse.ok) {
+            const data = await proprietaryResponse.json();
+            if (data && data.enableLogin !== null) {
+              console.log('[BackendStartup] Backend is ready (proprietary check), redirecting');
+              const redirectTo = sessionStorage.getItem('backendStartupRedirect') || '/';
+              sessionStorage.removeItem('backendStartupRedirect');
+
+              setTimeout(() => {
+                if (isMounted) {
+                  navigate(redirectTo, { replace: true });
+                }
+              }, 500);
+              return;
+            }
+          }
+        }
+
+        // Backend not ready yet, continue polling
+        if (response.status === 404 || response.status === 503) {
+          setPollAttempt(prev => prev + 1);
+          setStatusMessage(`Backend not ready (${response.status})`);
+        } else {
+          setPollAttempt(prev => prev + 1);
+          setStatusMessage(response.statusText || null);
+        }
+
+        // Schedule next poll (exponential backoff, max 5 seconds)
+        const delay = Math.min(1000 * Math.pow(1.5, pollAttempt), 5000);
+        timeoutId = setTimeout(checkBackendStatus, delay);
+      } catch (err) {
+        // Network error or backend not responding
+        if (!isMounted) return;
+
+        console.debug('[BackendStartup] Poll attempt failed:', err);
+        setPollAttempt(prev => prev + 1);
+        setStatusMessage(err instanceof Error ? err.message : null);
+
+        // Continue polling with backoff
+        const delay = Math.min(1000 * Math.pow(1.5, pollAttempt), 5000);
+        timeoutId = setTimeout(checkBackendStatus, delay);
+      }
+    };
+
+    // Start polling after a short delay to avoid race conditions
+    timeoutId = setTimeout(checkBackendStatus, 500);
+
+    // Cleanup on unmount
+    return () => {
+      isMounted = false;
+      if (timeoutId) clearTimeout(timeoutId);
+    };
+  }, [navigate, pollAttempt, BASE_PATH]);
+
+  return (
+    <AuthLayout>
+      {/* Header without title prop for custom styling */}
+      <div className="login-header">
+        <div className="login-header-logos">
+          <img src={`${BASE_PATH}/branding/StirlingPDFLogoBlackText.svg`} alt="Stirling PDF" className="login-logo-text" />
+        </div>
+      </div>
+
+      {/* Backend loading message */}
+      <div
+        className="auth-section"
+        style={{
+          padding: '1.5rem',
+          marginTop: '1rem',
+          borderRadius: '0.75rem',
+          backgroundColor: 'rgba(37, 99, 235, 0.08)',
+          border: '1px solid rgba(37, 99, 235, 0.2)',
+        }}
+      >
+        <p style={{ fontSize: '1.125rem', fontWeight: 600, marginBottom: '0.5rem', textAlign: 'center' }}>
+          {t('backendStartup.loadingTitle', 'Backend starting up')}
+        </p>
+        <p style={{ margin: 0, textAlign: 'center', color: 'rgba(15, 23, 42, 0.8)' }}>
+          {t('backendStartup.loadingMessage', 'The backend is currently starting up. This usually takes a few moments.')}
+        </p>
+
+        {/* Loading indicator */}
+        <div style={{ display: 'flex', justifyContent: 'center', marginTop: '1rem' }}>
+          <div style={{
+            width: '32px',
+            height: '32px',
+            border: '3px solid rgba(37, 99, 235, 0.2)',
+            borderTop: '3px solid rgba(37, 99, 235, 0.8)',
+            borderRadius: '50%',
+            animation: 'spin 1s linear infinite'
+          }} />
+        </div>
+
+        {statusMessage && (
+          <p style={{ marginTop: '0.75rem', fontSize: '0.875rem', textAlign: 'center', color: 'rgba(15, 23, 42, 0.6)' }}>
+            {statusMessage}
+          </p>
+        )}
+
+        {pollAttempt > 10 && (
+          <p style={{ marginTop: '1rem', fontSize: '0.875rem', textAlign: 'center', color: 'rgba(15, 23, 42, 0.7)' }}>
+            {t('backendStartup.takingLonger', 'This is taking longer than expected. The backend should be ready soon.')}
+          </p>
+        )}
+      </div>
+
+      {/* Add spinner animation */}
+      <style>{`
+        @keyframes spin {
+          to { transform: rotate(360deg); }
+        }
+      `}</style>
+    </AuthLayout>
+  );
+}
diff --git a/frontend/src/proprietary/routes/Landing.tsx b/frontend/src/proprietary/routes/Landing.tsx
index 165013e6fd..53d5e2b6e3 100644
--- a/frontend/src/proprietary/routes/Landing.tsx
+++ b/frontend/src/proprietary/routes/Landing.tsx
@@ -76,8 +76,13 @@ export default function Landing() {
   }
 
   // If login is disabled, show app directly (anonymous mode)
-  if (config?.enableLogin === false) {
-    console.debug('[Landing] Login disabled - showing app in anonymous mode');
+  // Check both the config AND sessionStorage flag (in case config is wrong)
+  const loginActuallyDisabled = sessionStorage.getItem('loginActuallyDisabled') === 'true';
+  if (config?.enableLogin === false || loginActuallyDisabled) {
+    console.debug('[Landing] Login disabled - showing app in anonymous mode', {
+      configSays: config?.enableLogin,
+      actuallyDisabled: loginActuallyDisabled
+    });
     return <HomePage />;
   }
 
diff --git a/frontend/src/proprietary/routes/Login.tsx b/frontend/src/proprietary/routes/Login.tsx
index e56d9faf90..505ef35842 100644
--- a/frontend/src/proprietary/routes/Login.tsx
+++ b/frontend/src/proprietary/routes/Login.tsx
@@ -4,6 +4,7 @@ import { springAuth } from '@app/auth/springAuthClient';
 import { useAuth } from '@app/auth/UseSession';
 import { useTranslation } from 'react-i18next';
 import { useDocumentMeta } from '@app/hooks/useDocumentMeta';
+import { useAppConfig } from '@app/contexts/AppConfigContext';
 import AuthLayout from '@app/routes/authShared/AuthLayout';
 
 // Import login components
@@ -19,6 +20,7 @@ export default function Login() {
   const navigate = useNavigate();
   const [searchParams] = useSearchParams();
   const { session, loading } = useAuth();
+  const { config, loading: configLoading } = useAppConfig();
   const { t } = useTranslation();
   const [isSigningIn, setIsSigningIn] = useState(false);
   const [error, setError] = useState<string | null>(null);
@@ -29,20 +31,91 @@ export default function Login() {
   const [enabledProviders, setEnabledProviders] = useState<string[]>([]);
   const [hasSSOProviders, setHasSSOProviders] = useState(false);
   const [_enableLogin, setEnableLogin] = useState<boolean | null>(null);
-  const [backendUnavailable, setBackendUnavailable] = useState(false);
-  const [backendStatusDetails, setBackendStatusDetails] = useState<string | null>(null);
+  const [backendCheckFailed, setBackendCheckFailed] = useState(false);
+  const [hasRedirected, setHasRedirected] = useState(false);
+
+  // Check AppConfig first - if login is disabled, redirect to home immediately
+  useEffect(() => {
+    if (!configLoading && config?.enableLogin === false && !hasRedirected) {
+      console.debug('[Login] Config loaded, login disabled - redirecting to home');
+      setHasRedirected(true);
+      navigate('/', { replace: true });
+    }
+  }, [config, configLoading, navigate, hasRedirected]);
 
   // Fetch enabled SSO providers and login config from backend
   useEffect(() => {
+    let isMounted = true;
+
+    // Don't fetch if config is still loading or if we know login is disabled
+    if (configLoading) {
+      console.debug('[Login] Waiting for config to load before fetching providers');
+      return;
+    }
+
+    if (config?.enableLogin === false) {
+      console.debug('[Login] Login disabled per config, skipping provider fetch');
+      return;
+    }
+
     const fetchProviders = async () => {
       try {
-        const response = await fetch(`${BASE_PATH}/api/v1/proprietary/ui-data/login`);
+        const response = await fetch(`${BASE_PATH}/api/v1/proprietary/ui-data/login`, {
+          cache: 'no-cache'
+        });
+
+        if (!isMounted) return;
 
         if (!response.ok) {
-          if (response.status === 404 || response.status === 503) {
-            console.warn(`[Login] Login config endpoint unavailable (status ${response.status})`);
-            setBackendUnavailable(true);
-            setBackendStatusDetails(response.statusText || null);
+          // 404 likely means security is disabled (non-proprietary backend)
+          // Check the general status endpoint to see if backend is up
+          if (response.status === 404) {
+            console.debug('[Login] Proprietary endpoint not found - checking if security is disabled (this is expected behavior when security is disabled)');
+
+            try {
+              const statusResponse = await fetch(`${BASE_PATH}/api/v1/info/status`, {
+                cache: 'no-cache'
+              });
+
+              if (statusResponse.ok) {
+                // Backend is up, but security is disabled
+                // This means the config is wrong - login is actually disabled
+                console.debug('[Login] Backend is up but security disabled - redirecting to home');
+
+                // Set a flag in sessionStorage so Landing knows login is actually disabled
+                sessionStorage.setItem('loginActuallyDisabled', 'true');
+
+                navigate('/', { replace: true });
+                return;
+              }
+            } catch (statusErr) {
+              console.debug('[Login] Status check failed, backend may be starting up');
+            }
+
+            // Backend is not responding properly - redirect to startup page
+            console.debug('[Login] Backend starting up - redirecting to backend startup page');
+            setBackendCheckFailed(true);
+            sessionStorage.setItem('backendStartupRedirect', window.location.pathname + window.location.search);
+
+            setTimeout(() => {
+              if (isMounted) {
+                navigate('/backend-startup', { replace: true });
+              }
+            }, 300);
+            return;
+          }
+
+          // 503 means backend is starting up
+          if (response.status === 503) {
+            console.warn('[Login] Backend unavailable (503) - redirecting to backend startup');
+            setBackendCheckFailed(true);
+            sessionStorage.setItem('backendStartupRedirect', window.location.pathname + window.location.search);
+
+            setTimeout(() => {
+              if (isMounted) {
+                navigate('/backend-startup', { replace: true });
+              }
+            }, 300);
             return;
           }
 
@@ -52,22 +125,45 @@ export default function Login() {
 
         const data = await response.json();
 
+        if (!isMounted) return;
+
         if (!data || data.enableLogin === null) {
-          console.warn('[Login] Login config returned empty or null data - showing backend unavailable message');
-          setBackendUnavailable(true);
-          setBackendStatusDetails(null);
+          console.warn('[Login] Login config returned empty or null data - checking backend status');
+
+          // Check if backend is actually up before assuming it's starting
+          try {
+            const statusResponse = await fetch(`${BASE_PATH}/api/v1/info/status`, {
+              cache: 'no-cache'
+            });
+
+            if (statusResponse.ok) {
+              // Backend is up but returning invalid data - redirect to home as fallback
+              console.debug('[Login] Backend up but invalid login data - redirecting to home');
+              navigate('/', { replace: true });
+              return;
+            }
+          } catch (statusErr) {
+            console.debug('[Login] Status check failed');
+          }
+
+          setBackendCheckFailed(true);
+          sessionStorage.setItem('backendStartupRedirect', window.location.pathname + window.location.search);
+
+          setTimeout(() => {
+            if (isMounted) {
+              navigate('/backend-startup', { replace: true });
+            }
+          }, 300);
           return;
         }
 
         // Check if login is disabled - if so, redirect to home
         if (data.enableLogin === false) {
           console.debug('[Login] Login disabled, redirecting to home');
-          navigate('/');
+          navigate('/', { replace: true });
           return;
         }
 
-        setBackendUnavailable(false);
-        setBackendStatusDetails(null);
         setEnableLogin(data.enableLogin ?? true);
 
         // Extract provider IDs from the providerList map
@@ -77,13 +173,26 @@ export default function Login() {
           .filter((id): id is string => id !== undefined);
         setEnabledProviders(providerIds);
       } catch (err) {
+        if (!isMounted) return;
+
         console.error('[Login] Failed to fetch enabled providers:', err);
-        setBackendUnavailable(true);
-        setBackendStatusDetails(err instanceof Error ? err.message : null);
+        setBackendCheckFailed(true);
+        sessionStorage.setItem('backendStartupRedirect', window.location.pathname + window.location.search);
+
+        setTimeout(() => {
+          if (isMounted) {
+            navigate('/backend-startup', { replace: true });
+          }
+        }, 300);
       }
     };
+
     fetchProviders();
-  }, [navigate]);
+
+    return () => {
+      isMounted = false;
+    };
+  }, [navigate, BASE_PATH, config, configLoading]);
 
   // Update hasSSOProviders and showEmailForm when enabledProviders changes
   useEffect(() => {
@@ -148,6 +257,23 @@ export default function Login() {
     return <LoggedInState />;
   }
 
+  // Show loading while checking backend, config, or redirecting
+  // Also show loading if we know login is disabled (we're about to redirect)
+  if (loading || configLoading || backendCheckFailed || hasRedirected || (!configLoading && config?.enableLogin === false)) {
+    return (
+      <AuthLayout>
+        <div style={{ minHeight: '300px', display: 'flex', alignItems: 'center', justifyContent: 'center' }}>
+          <div className="text-center">
+            <div className="animate-spin rounded-full h-8 w-8 border-b-2 border-blue-600 mx-auto mb-3"></div>
+            <div className="text-gray-600">
+              Loading...
+            </div>
+          </div>
+        </div>
+      </AuthLayout>
+    );
+  }
+
   const signInWithProvider = async (provider: 'github' | 'google' | 'apple' | 'azure' | 'keycloak' | 'oidc') => {
     try {
       setIsSigningIn(true);
@@ -211,97 +337,68 @@ export default function Login() {
   //   navigate('/auth/reset');
   // };
 
-  const loginHeaderTitle = backendUnavailable ? undefined : (t('login.login') || 'Sign in');
-
   return (
     <AuthLayout>
-      <LoginHeader title={loginHeaderTitle} />
+      <LoginHeader title={t('login.login') || 'Sign in'} />
 
-      {backendUnavailable ? (
-        <div
-          className="auth-section"
-          style={{
-            padding: '1.5rem',
-            marginTop: '1rem',
-            borderRadius: '0.75rem',
-            backgroundColor: 'rgba(37, 99, 235, 0.08)',
-            border: '1px solid rgba(37, 99, 235, 0.2)',
-          }}
-        >
-          <p style={{ fontSize: '1.125rem', fontWeight: 600, marginBottom: '0.5rem', textAlign: 'center' }}>
-            {t('login.backendLoadingTitle', 'Backend starting up')}
+      {/* Success message */}
+      {successMessage && (
+        <div style={{
+          padding: '1rem',
+          marginBottom: '1rem',
+          backgroundColor: 'rgba(34, 197, 94, 0.1)',
+          border: '1px solid rgba(34, 197, 94, 0.3)',
+          borderRadius: '0.5rem',
+          color: '#16a34a'
+        }}>
+          <p style={{ margin: 0, fontSize: '0.875rem', textAlign: 'center' }}>
+            {successMessage}
           </p>
-          <p style={{ margin: 0, textAlign: 'center', color: 'rgba(15, 23, 42, 0.8)' }}>
-            {t('login.backendLoadingMessage', 'Backend is currently loading and/or not started. Please wait a few moments and try again.')}
-          </p>
-          {backendStatusDetails && (
-            <p style={{ marginTop: '0.75rem', fontSize: '0.875rem', textAlign: 'center', color: 'rgba(15, 23, 42, 0.6)' }}>
-              {backendStatusDetails}
-            </p>
-          )}
         </div>
-      ) : (
-        <>
-          {/* Success message */}
-          {successMessage && (
-            <div style={{
-              padding: '1rem',
-              marginBottom: '1rem',
-              backgroundColor: 'rgba(34, 197, 94, 0.1)',
-              border: '1px solid rgba(34, 197, 94, 0.3)',
-              borderRadius: '0.5rem',
-              color: '#16a34a'
-            }}>
-              <p style={{ margin: 0, fontSize: '0.875rem', textAlign: 'center' }}>
-                {successMessage}
-              </p>
-            </div>
-          )}
+      )}
 
-          <ErrorMessage error={error} />
+      <ErrorMessage error={error} />
 
-          {/* OAuth first */}
-          <OAuthButtons
-            onProviderClick={signInWithProvider}
+      {/* OAuth first */}
+      <OAuthButtons
+        onProviderClick={signInWithProvider}
+        isSubmitting={isSigningIn}
+        layout="vertical"
+        enabledProviders={enabledProviders}
+      />
+
+      {/* Divider between OAuth and Email - only show if SSO is available */}
+      {hasSSOProviders && (
+        <DividerWithText text={t('signup.or', 'or')} respondsToDarkMode={false} opacity={0.4} />
+      )}
+
+      {/* Sign in with email button - only show if SSO providers exist */}
+      {hasSSOProviders && !showEmailForm && (
+        <div className="auth-section">
+          <button
+            type="button"
+            onClick={() => setShowEmailForm(true)}
+            disabled={isSigningIn}
+            className="w-full px-4 py-[0.75rem] rounded-[0.625rem] text-base font-semibold mb-2 cursor-pointer border-0 disabled:opacity-50 disabled:cursor-not-allowed auth-cta-button"
+          >
+            {t('login.useEmailInstead', 'Login with email')}
+          </button>
+        </div>
+      )}
+
+      {/* Email form - show by default if no SSO, or when button clicked */}
+      {showEmailForm && (
+        <div style={{ marginTop: hasSSOProviders ? '1rem' : '0' }}>
+          <EmailPasswordForm
+            email={email}
+            password={password}
+            setEmail={setEmail}
+            setPassword={setPassword}
+            onSubmit={signInWithEmail}
             isSubmitting={isSigningIn}
-            layout="vertical"
-            enabledProviders={enabledProviders}
+            submitButtonText={isSigningIn ? (t('login.loggingIn') || 'Signing in...') : (t('login.login') || 'Sign in')}
           />
-
-          {/* Divider between OAuth and Email - only show if SSO is available */}
-          {hasSSOProviders && (
-            <DividerWithText text={t('signup.or', 'or')} respondsToDarkMode={false} opacity={0.4} />
-          )}
-
-          {/* Sign in with email button - only show if SSO providers exist */}
-          {hasSSOProviders && !showEmailForm && (
-            <div className="auth-section">
-              <button
-                type="button"
-                onClick={() => setShowEmailForm(true)}
-                disabled={isSigningIn}
-                className="w-full px-4 py-[0.75rem] rounded-[0.625rem] text-base font-semibold mb-2 cursor-pointer border-0 disabled:opacity-50 disabled:cursor-not-allowed auth-cta-button"
-              >
-                {t('login.useEmailInstead', 'Login with email')}
-              </button>
-            </div>
-          )}
-
-          {/* Email form - show by default if no SSO, or when button clicked */}
-          {showEmailForm && (
-            <div style={{ marginTop: hasSSOProviders ? '1rem' : '0' }}>
-              <EmailPasswordForm
-                email={email}
-                password={password}
-                setEmail={setEmail}
-                setPassword={setPassword}
-                onSubmit={signInWithEmail}
-                isSubmitting={isSigningIn}
-                submitButtonText={isSigningIn ? (t('login.loggingIn') || 'Signing in...') : (t('login.login') || 'Sign in')}
-              />
-            </div>
-          )}
-        </>
+        </div>
       )}
 
     </AuthLayout>