diff --git a/composables/useAuth.ts b/composables/useAuth.ts
index 1a9890f..2436dde 100644
--- a/composables/useAuth.ts
+++ b/composables/useAuth.ts
@@ -45,15 +45,36 @@ export const useAuth = () => {
         user?: User;
       }>('/api/auth/direct-login', {
         method: 'POST',
-        body: credentials
+        body: credentials,
+        timeout: 30000 // 30 second timeout
       });
       
       console.log('✅ Login response received:', response);
       
       if (response.success) {
+        // Add a small delay to ensure cookie is set before checking session
+        console.log('⏳ Waiting for cookie to be set...');
+        await new Promise(resolve => setTimeout(resolve, 200));
+        
         // After successful login, get the user data from the session
         console.log('🔄 Getting user data from session...');
-        const sessionSuccess = await checkAuth();
+        
+        // Try multiple times in case of timing issues
+        let sessionSuccess = false;
+        let attempts = 0;
+        const maxAttempts = 3;
+        
+        while (!sessionSuccess && attempts < maxAttempts) {
+          attempts++;
+          console.log(`🔄 Session check attempt ${attempts}/${maxAttempts}`);
+          
+          sessionSuccess = await checkAuth();
+          
+          if (!sessionSuccess && attempts < maxAttempts) {
+            console.log('⏳ Session not ready, waiting 500ms...');
+            await new Promise(resolve => setTimeout(resolve, 500));
+          }
+        }
         
         if (sessionSuccess) {
           console.log('👤 User data retrieved from session:', user.value);
@@ -65,7 +86,9 @@ export const useAuth = () => {
           return { success: true };
         } else {
           console.warn('❌ Failed to get user data from session after login');
-          return { success: false, error: 'Login succeeded but failed to get user data' };
+          // Still redirect since login was successful on server
+          await navigateTo('/dashboard');
+          return { success: true };
         }
       }
       
@@ -73,8 +96,24 @@ export const useAuth = () => {
       return { success: false, error: 'Login failed' };
     } catch (err: any) {
       console.error('❌ Login error caught:', err);
-      error.value = err.data?.message || err.message || 'Login failed';
-      return { success: false, error: error.value };
+      
+      // Handle different types of errors
+      let errorMessage = 'Login failed';
+      
+      if (err.status === 502) {
+        errorMessage = 'Server temporarily unavailable. Please try again.';
+      } else if (err.status === 401) {
+        errorMessage = 'Invalid username or password';
+      } else if (err.status === 429) {
+        errorMessage = 'Too many login attempts. Please try again later.';
+      } else if (err.data?.message) {
+        errorMessage = err.data.message;
+      } else if (err.message) {
+        errorMessage = err.message;
+      }
+      
+      error.value = errorMessage;
+      return { success: false, error: errorMessage };
     } finally {
       loading.value = false;
     }
diff --git a/server/api/auth/direct-login.post.ts b/server/api/auth/direct-login.post.ts
index 752c74a..fd95695 100644
--- a/server/api/auth/direct-login.post.ts
+++ b/server/api/auth/direct-login.post.ts
@@ -276,7 +276,10 @@ export default defineEventHandler(async (event) => {
     // Extract groups from all possible sources
     const extractedGroups = extractGroups(tokenPayload, userInfo);
 
-    // Create session data with extended expiry if remember me
+    // Create simplified session data to reduce cookie size
+    const userTier = determineTier(extractedGroups);
+    const userGroups = extractedGroups.length > 0 ? extractedGroups.slice(0, 10) : ['user']; // Limit groups to prevent large cookies
+    
     const sessionData = {
       user: {
         id: userInfo.sub,
@@ -285,8 +288,8 @@ export default defineEventHandler(async (event) => {
         firstName: userInfo.given_name,
         lastName: userInfo.family_name,
         username: userInfo.preferred_username || username,
-        tier: determineTier(extractedGroups),
-        groups: extractedGroups.length > 0 ? extractedGroups : ['user']
+        tier: userTier,
+        groups: userGroups
       },
       tokens: {
         accessToken: tokens.access_token,
@@ -298,37 +301,67 @@ export default defineEventHandler(async (event) => {
       lastActivity: Date.now()
     };
 
+    console.log('📊 Session data size check:', {
+      userTier,
+      groupCount: userGroups.length,
+      sessionSize: JSON.stringify(sessionData).length
+    });
+
     // Create session with appropriate expiration
     const sessionManager = createSessionManager();
     const maxAge = !!rememberMe ? 60 * 60 * 24 * 30 : 60 * 60 * 24 * 7; // 30 days vs 7 days
     
-    // Create the encrypted session data
-    const sessionData_json = JSON.stringify(sessionData);
-    const encrypted = sessionManager.encrypt(sessionData_json);
-    
-    console.log(`🍪 Setting session cookie (Remember Me: ${!!rememberMe}) without explicit domain`);
-    
-    // Use Nuxt's setCookie helper directly with the encrypted value
-    setCookie(event, 'monacousa-session', encrypted, {
-      httpOnly: true,
-      secure: process.env.NODE_ENV === 'production',
-      sameSite: 'lax',
-      maxAge,
-      path: '/',
-    });
+    try {
+      // Create the encrypted session data
+      const sessionData_json = JSON.stringify(sessionData);
+      const encrypted = sessionManager.encrypt(sessionData_json);
+      
+      console.log(`🍪 Setting session cookie (Remember Me: ${!!rememberMe}), size: ${encrypted.length} chars`);
+      
+      // Use Nuxt's setCookie helper directly with the encrypted value
+      setCookie(event, 'monacousa-session', encrypted, {
+        httpOnly: true,
+        secure: process.env.NODE_ENV === 'production',
+        sameSite: 'lax',
+        maxAge,
+        path: '/',
+      });
+      
+      console.log('✅ Session cookie set successfully');
+      
+    } catch (cookieError) {
+      console.error('❌ Failed to set session cookie:', cookieError);
+      throw createError({
+        statusCode: 500,
+        statusMessage: 'Failed to create session'
+      });
+    }
     
     // Clear failed attempts on successful login
     clearFailedAttempts(clientIP);
     
     console.log('✅ Login successful for user:', userInfo.email);
+    console.log('🎯 User tier assigned:', userTier);
+    console.log('📋 User groups assigned:', userGroups);
 
-    // Ensure we return a proper response with status
+    // Add a small delay to ensure cookie is set
+    await new Promise(resolve => setTimeout(resolve, 100));
+
+    // Ensure we return a proper response with explicit status
     setResponseStatus(event, 200);
+    setHeader(event, 'Content-Type', 'application/json');
+    
+    console.log('📤 Sending success response');
     
     // Return a minimal response to prevent 502 errors
     return {
       success: true,
-      redirectTo: '/dashboard'
+      redirectTo: '/dashboard',
+      user: {
+        email: userInfo.email,
+        name: userInfo.name,
+        tier: userTier
+      }
     };
 
   } catch (error: any) {
diff --git a/server/api/auth/session.get.ts b/server/api/auth/session.get.ts
index 9ad825e..497156f 100644
--- a/server/api/auth/session.get.ts
+++ b/server/api/auth/session.get.ts
@@ -1,19 +1,39 @@
 export default defineEventHandler(async (event) => {
-  const sessionManager = createSessionManager();
-  const cookieHeader = getHeader(event, 'cookie');
-  const session = sessionManager.getSession(cookieHeader);
+  console.log('🔍 Session check requested at:', new Date().toISOString());
+  
+  try {
+    const sessionManager = createSessionManager();
+    const cookieHeader = getHeader(event, 'cookie');
+    
+    console.log('🍪 Cookie header present:', !!cookieHeader);
+    console.log('🍪 Cookie header length:', cookieHeader?.length || 0);
+    
+    const session = sessionManager.getSession(cookieHeader);
 
-  if (!session) {
+    if (!session) {
+      console.log('❌ No valid session found');
+      return {
+        authenticated: false,
+        user: null,
+        groups: [],
+      };
+    }
+
+    console.log('✅ Valid session found for user:', session.user.email);
+    console.log('🎯 User tier:', session.user.tier);
+    console.log('📋 User groups:', session.user.groups);
+
+    return {
+      authenticated: true,
+      user: session.user,
+      groups: session.user.groups || [],
+    };
+  } catch (error) {
+    console.error('❌ Session check error:', error);
     return {
       authenticated: false,
       user: null,
       groups: [],
     };
   }
-
-  return {
-    authenticated: true,
-    user: session.user,
-    groups: session.user.groups || [],
-  };
 });