diff --git a/apps/ui/src/components/views/login-view.tsx b/apps/ui/src/components/views/login-view.tsx
index c619f1f2..0bcfbece 100644
--- a/apps/ui/src/components/views/login-view.tsx
+++ b/apps/ui/src/components/views/login-view.tsx
@@ -3,17 +3,26 @@
  *
  * Prompts user to enter the API key shown in server console.
  * On successful login, sets an HTTP-only session cookie.
+ *
+ * On mount, verifies if an existing session is valid using exponential backoff.
+ * This handles cases where server live reloads kick users back to login
+ * even though their session is still valid.
  */
 
-import { useState } from 'react';
+import { useState, useEffect, useRef } from 'react';
 import { useNavigate } from '@tanstack/react-router';
-import { login } from '@/lib/http-api-client';
+import { login, verifySession } from '@/lib/http-api-client';
 import { Button } from '@/components/ui/button';
 import { Input } from '@/components/ui/input';
 import { KeyRound, AlertCircle, Loader2 } from 'lucide-react';
 import { useAuthStore } from '@/store/auth-store';
 import { useSetupStore } from '@/store/setup-store';
 
+/**
+ * Delay helper for exponential backoff
+ */
+const delay = (ms: number) => new Promise((resolve) => setTimeout(resolve, ms));
+
 export function LoginView() {
   const navigate = useNavigate();
   const setAuthState = useAuthStore((s) => s.setAuthState);
@@ -21,6 +30,45 @@ export function LoginView() {
   const [apiKey, setApiKey] = useState('');
   const [error, setError] = useState<string | null>(null);
   const [isLoading, setIsLoading] = useState(false);
+  const [isCheckingSession, setIsCheckingSession] = useState(true);
+  const sessionCheckRef = useRef(false);
+
+  // Check for existing valid session on mount with exponential backoff
+  useEffect(() => {
+    // Prevent duplicate checks in strict mode
+    if (sessionCheckRef.current) return;
+    sessionCheckRef.current = true;
+
+    const checkExistingSession = async () => {
+      const maxRetries = 5;
+      const baseDelay = 500; // Start with 500ms
+
+      for (let attempt = 0; attempt < maxRetries; attempt++) {
+        try {
+          const isValid = await verifySession();
+          if (isValid) {
+            // Session is valid, redirect to the main app
+            setAuthState({ isAuthenticated: true, authChecked: true });
+            navigate({ to: setupComplete ? '/' : '/setup' });
+            return;
+          }
+          // Session is invalid, no need to retry - show login form
+          break;
+        } catch {
+          // Network error or server not ready, retry with exponential backoff
+          if (attempt < maxRetries - 1) {
+            const waitTime = baseDelay * Math.pow(2, attempt); // 500, 1000, 2000, 4000, 8000ms
+            await delay(waitTime);
+          }
+        }
+      }
+
+      // Session check complete (either invalid or all retries exhausted)
+      setIsCheckingSession(false);
+    };
+
+    checkExistingSession();
+  }, [navigate, setAuthState, setupComplete]);
 
   const handleSubmit = async (e: React.FormEvent) => {
     e.preventDefault();
@@ -45,6 +93,18 @@ export function LoginView() {
     }
   };
 
+  // Show loading state while checking existing session
+  if (isCheckingSession) {
+    return (
+      <div className="flex min-h-screen items-center justify-center bg-background p-4">
+        <div className="text-center space-y-4">
+          <Loader2 className="h-8 w-8 animate-spin mx-auto text-primary" />
+          <p className="text-sm text-muted-foreground">Checking session...</p>
+        </div>
+      </div>
+    );
+  }
+
   return (
     <div className="flex min-h-screen items-center justify-center bg-background p-4">
       <div className="w-full max-w-md space-y-8">
diff --git a/apps/ui/src/components/views/settings-view/api-keys/api-keys-section.tsx b/apps/ui/src/components/views/settings-view/api-keys/api-keys-section.tsx
index e0261e97..e6ab828e 100644
--- a/apps/ui/src/components/views/settings-view/api-keys/api-keys-section.tsx
+++ b/apps/ui/src/components/views/settings-view/api-keys/api-keys-section.tsx
@@ -1,7 +1,7 @@
 import { useAppStore } from '@/store/app-store';
 import { useSetupStore } from '@/store/setup-store';
 import { Button } from '@/components/ui/button';
-import { Key, CheckCircle2, Settings, Trash2, Loader2 } from 'lucide-react';
+import { Key, CheckCircle2, Trash2, Loader2 } from 'lucide-react';
 import { ApiKeyField } from './api-key-field';
 import { buildProviderConfigs } from '@/config/api-providers';
 import { SecurityNotice } from './security-notice';
@@ -10,13 +10,11 @@ import { cn } from '@/lib/utils';
 import { useState, useCallback } from 'react';
 import { getElectronAPI } from '@/lib/electron';
 import { toast } from 'sonner';
-import { useNavigate } from '@tanstack/react-router';
 
 export function ApiKeysSection() {
   const { apiKeys, setApiKeys } = useAppStore();
-  const { claudeAuthStatus, setClaudeAuthStatus, setSetupComplete } = useSetupStore();
+  const { claudeAuthStatus, setClaudeAuthStatus } = useSetupStore();
   const [isDeletingAnthropicKey, setIsDeletingAnthropicKey] = useState(false);
-  const navigate = useNavigate();
 
   const { providerConfigParams, handleSave, saved } = useApiKeyManagement();
 
@@ -51,12 +49,6 @@ export function ApiKeysSection() {
     }
   }, [apiKeys, setApiKeys, claudeAuthStatus, setClaudeAuthStatus]);
 
-  // Open setup wizard
-  const openSetupWizard = useCallback(() => {
-    setSetupComplete(false);
-    navigate({ to: '/setup' });
-  }, [setSetupComplete, navigate]);
-
   return (
     <div
       className={cn(
@@ -111,16 +103,6 @@ export function ApiKeysSection() {
             )}
           </Button>
 
-          <Button
-            onClick={openSetupWizard}
-            variant="outline"
-            className="h-10 border-border"
-            data-testid="run-setup-wizard"
-          >
-            <Settings className="w-4 h-4 mr-2" />
-            Run Setup Wizard
-          </Button>
-
           {apiKeys.anthropic && (
             <Button
               onClick={deleteAnthropicKey}