diff --git a/lib/core/auth/auth_state_manager.dart b/lib/core/auth/auth_state_manager.dart
index a5f58fc..6883d20 100644
--- a/lib/core/auth/auth_state_manager.dart
+++ b/lib/core/auth/auth_state_manager.dart
@@ -187,6 +187,23 @@ class AuthStateManager extends _$AuthStateManager {
 
       if (token != null && token.isNotEmpty) {
         DebugLogger.auth('Found stored token during initialization');
+
+        // Check if stored token is an API key - force logout if so
+        if (TokenValidator.isApiKey(token)) {
+          DebugLogger.auth('Detected API key token, forcing logout');
+          await storage.deleteAuthToken();
+          await storage.deleteSavedCredentials();
+          _update(
+            (current) => current.copyWith(
+              status: AuthStatus.credentialError,
+              error: 'apiKeyNoLongerSupported',
+              isLoading: false,
+              clearToken: true,
+            ),
+          );
+          return;
+        }
+
         // Fast path: trust token format to avoid blocking startup on network
         final formatOk = _isValidTokenFormat(token);
         if (formatOk) {
@@ -270,7 +287,8 @@ class AuthStateManager extends _$AuthStateManager {
     }
   }
 
-  /// Perform login with API key
+  /// Perform login with JWT token
+  /// Note: API keys (sk-...) are not supported for streaming.
   Future<bool> loginWithApiKey(
     String apiKey, {
     bool rememberCredentials = false,
@@ -284,9 +302,16 @@ class AuthStateManager extends _$AuthStateManager {
     );
 
     try {
-      // Validate API key format
+      // Validate token is not empty
       if (apiKey.trim().isEmpty) {
-        throw Exception('API key cannot be empty');
+        throw Exception('Token cannot be empty');
+      }
+
+      final tokenStr = apiKey.trim();
+
+      // Reject API keys - they don't support streaming
+      if (TokenValidator.isApiKey(tokenStr)) {
+        throw Exception('apiKeyNotSupported');
       }
 
       // Ensure API service is available
@@ -296,12 +321,9 @@ class AuthStateManager extends _$AuthStateManager {
         throw Exception('No server connection available');
       }
 
-      // Use API key directly as Bearer token
-      final tokenStr = apiKey.trim();
-
-      // Validate token format (consistent with credentials method)
+      // Validate token format
       if (!_isValidTokenFormat(tokenStr)) {
-        throw Exception('Invalid API key format');
+        throw Exception('Invalid token format');
       }
 
       // Update API service with the API key
@@ -315,16 +337,15 @@ class AuthStateManager extends _$AuthStateManager {
         final storage = ref.read(optimizedStorageServiceProvider);
         await storage.saveAuthToken(tokenStr);
 
-        // Save API key if requested (for convenience, though less secure than credentials)
+        // Save JWT token if requested
         if (rememberCredentials) {
           final activeServer = await ref.read(activeServerProvider.future);
           if (activeServer != null) {
-            // Store API key as a special credential type
+            // Store JWT as a special credential type
             await storage.saveCredentials(
               serverId: activeServer.id,
-              username:
-                  'api_key_user', // Special username to indicate API key auth
-              password: tokenStr, // Store API key in password field
+              username: 'jwt_user', // Special username to indicate JWT auth
+              password: tokenStr, // Store JWT in password field
             );
           }
         }
@@ -348,11 +369,11 @@ class AuthStateManager extends _$AuthStateManager {
         _loadUserData();
         _prefetchConversations();
 
-        DebugLogger.auth('API key login successful');
+        DebugLogger.auth('JWT token login successful');
         return true;
       } catch (e) {
-        // If user fetch fails, the API key might be invalid
-        throw Exception('Invalid API key or insufficient permissions');
+        // If user fetch fails, the token might be invalid
+        throw Exception('Invalid token or insufficient permissions');
       }
     } catch (e, stack) {
       DebugLogger.error(
@@ -561,8 +582,8 @@ class AuthStateManager extends _$AuthStateManager {
       }
 
       // Attempt login (detect API key vs normal credentials)
-      if (username == 'api_key_user') {
-        // This is a saved API key
+      if (username == 'api_key_user' || username == 'jwt_user') {
+        // This is a saved JWT token (or legacy API key)
         return await loginWithApiKey(password, rememberCredentials: false);
       } else {
         // Normal username/password credentials
diff --git a/lib/core/auth/token_validator.dart b/lib/core/auth/token_validator.dart
index 84e4355..08093bc 100644
--- a/lib/core/auth/token_validator.dart
+++ b/lib/core/auth/token_validator.dart
@@ -6,7 +6,15 @@ import '../utils/debug_logger.dart';
 class TokenValidator {
   static const Duration _validationTimeout = Duration(seconds: 5);
 
-  /// Validate token format (supports both JWT and API key formats)
+  /// Check if token is an API key format (sk-, api-, key-)
+  /// API keys are not supported for streaming.
+  static bool isApiKey(String token) {
+    return token.startsWith('sk-') ||
+        token.startsWith('api-') ||
+        token.startsWith('key-');
+  }
+
+  /// Validate token format (JWT tokens only - API keys not supported)
   static TokenValidationResult validateTokenFormat(String token) {
     try {
       // Basic format check
@@ -14,15 +22,11 @@ class TokenValidator {
         return TokenValidationResult.invalid('Token too short');
       }
 
-      // Check if it's an API key format (starts with sk- or similar)
-      if (token.startsWith('sk-') ||
-          token.startsWith('api-') ||
-          token.startsWith('key-')) {
-        // API key format - validate differently
-        if (token.length < 20) {
-          return TokenValidationResult.invalid('API key too short');
-        }
-        return TokenValidationResult.valid('API key format valid');
+      // Reject API keys - they don't support streaming
+      if (isApiKey(token)) {
+        return TokenValidationResult.apiKeyNotSupported(
+          'API keys are not supported. Please use a JWT token.',
+        );
       }
 
       // Check if it looks like a JWT (has at least 2 dots)
@@ -209,6 +213,9 @@ class TokenValidationResult {
   const TokenValidationResult.networkError(String message)
     : this._(false, TokenValidationStatus.networkError, message);
 
+  const TokenValidationResult.apiKeyNotSupported(String message)
+    : this._(false, TokenValidationStatus.apiKeyNotSupported, message);
+
   final bool isValid;
   final TokenValidationStatus status;
   final String message;
@@ -218,6 +225,8 @@ class TokenValidationResult {
   bool get isExpired => status == TokenValidationStatus.expired;
   bool get isExpiringSoon => status == TokenValidationStatus.expiringSoon;
   bool get hasNetworkError => status == TokenValidationStatus.networkError;
+  bool get isApiKeyNotSupported =>
+      status == TokenValidationStatus.apiKeyNotSupported;
 
   @override
   String toString() =>
@@ -230,6 +239,7 @@ enum TokenValidationStatus {
   expired,
   expiringSoon,
   networkError,
+  apiKeyNotSupported,
 }
 
 /// Cache for token validation results
diff --git a/lib/core/router/app_router.dart b/lib/core/router/app_router.dart
index 5b51590..77dd499 100644
--- a/lib/core/router/app_router.dart
+++ b/lib/core/router/app_router.dart
@@ -62,6 +62,14 @@ class RouterNotifier extends ChangeNotifier {
     final reviewerMode = ref.read(reviewerModeProvider);
     final activeServerAsync = ref.read(activeServerProvider);
 
+    // Check for API key forced logout first - redirect to authentication
+    final authSnapshot = ref
+        .read(authStateManagerProvider)
+        .maybeWhen(data: (s) => s, orElse: () => null);
+    if (authSnapshot?.error?.contains('apiKey') == true) {
+      return location == Routes.authentication ? null : Routes.authentication;
+    }
+
     if (reviewerMode) {
       // Stay on whatever route if already in chat; otherwise go to chat
       if (location == Routes.chat) return null;
diff --git a/lib/features/auth/views/authentication_page.dart b/lib/features/auth/views/authentication_page.dart
index 55b0f8a..9150c77 100644
--- a/lib/features/auth/views/authentication_page.dart
+++ b/lib/features/auth/views/authentication_page.dart
@@ -43,6 +43,23 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
   void initState() {
     super.initState();
     _loadSavedCredentials();
+    // Check for auth errors (e.g., forced logout due to API key)
+    WidgetsBinding.instance.addPostFrameCallback((_) {
+      _checkAuthStateError();
+    });
+  }
+
+  void _checkAuthStateError() {
+    final authState = ref.read(authStateManagerProvider).asData?.value;
+    if (authState?.error != null && authState!.error!.isNotEmpty) {
+      setState(() {
+        _loginError = _formatLoginError(authState.error!);
+        // Switch to token tab if the error is about API keys
+        if (authState.error!.contains('apiKey')) {
+          _useApiKey = true;
+        }
+      });
+    }
   }
 
   Future<void> _loadSavedCredentials() async {
@@ -127,16 +144,21 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
   }
 
   String _formatLoginError(String error) {
-    if (error.contains('401') || error.contains('Unauthorized')) {
-      return AppLocalizations.of(context)!.invalidCredentials;
+    final l10n = AppLocalizations.of(context)!;
+    if (error.contains('apiKeyNotSupported')) {
+      return l10n.apiKeyNotSupported;
+    } else if (error.contains('apiKeyNoLongerSupported')) {
+      return l10n.apiKeyNoLongerSupported;
+    } else if (error.contains('401') || error.contains('Unauthorized')) {
+      return l10n.invalidCredentials;
     } else if (error.contains('redirect')) {
-      return AppLocalizations.of(context)!.serverRedirectingHttps;
+      return l10n.serverRedirectingHttps;
     } else if (error.contains('SocketException')) {
-      return AppLocalizations.of(context)!.unableToConnectServer;
+      return l10n.unableToConnectServer;
     } else if (error.contains('timeout')) {
-      return AppLocalizations.of(context)!.requestTimedOut;
+      return l10n.requestTimedOut;
     }
-    return AppLocalizations.of(context)!.genericSignInFailed;
+    return l10n.genericSignInFailed;
   }
 
   @override
diff --git a/lib/l10n/app_de.arb b/lib/l10n/app_de.arb
index 7acb46e..5455e87 100644
--- a/lib/l10n/app_de.arb
+++ b/lib/l10n/app_de.arb
@@ -230,6 +230,7 @@
   "enterToken": "Gib dein JWT-Token ein",
   "tokenHint": "Hole das JWT-Token aus den OpenWebUI-Einstellungen. API-Schlüssel (sk-...) werden für Streaming nicht unterstützt.",
   "apiKeyNotSupported": "API-Schlüssel (sk-...) werden nicht unterstützt. Bitte verwende stattdessen ein JWT-Token.",
+  "apiKeyNoLongerSupported": "Du wurdest abgemeldet, da API-Schlüssel nicht mehr unterstützt werden. Bitte melde dich mit einem JWT-Token aus den OpenWebUI-Einstellungen an.",
   "tokenTooShort": "Token ist zu kurz",
   "signingIn": "Anmeldung läuft...",
   "advancedSettings": "Erweiterte Einstellungen",
diff --git a/lib/l10n/app_en.arb b/lib/l10n/app_en.arb
index 425cc08..1a9dfbd 100644
--- a/lib/l10n/app_en.arb
+++ b/lib/l10n/app_en.arb
@@ -1024,6 +1024,10 @@
   "@apiKeyNotSupported": {
     "description": "Error message when user tries to use an API key instead of JWT token."
   },
+  "apiKeyNoLongerSupported": "You were logged out because API keys are no longer supported. Please sign in with a JWT token from OpenWebUI settings.",
+  "@apiKeyNoLongerSupported": {
+    "description": "Error message shown when user is forced logged out due to using an API key."
+  },
   "tokenTooShort": "Token is too short",
   "@tokenTooShort": {
     "description": "Error message when token is too short."
diff --git a/lib/l10n/app_es.arb b/lib/l10n/app_es.arb
index 1a01220..b8128d7 100644
--- a/lib/l10n/app_es.arb
+++ b/lib/l10n/app_es.arb
@@ -230,6 +230,7 @@
   "enterToken": "Ingresa tu token JWT",
   "tokenHint": "Obtén el token JWT desde la configuración de OpenWebUI. Las claves API (sk-...) no son compatibles con streaming.",
   "apiKeyNotSupported": "Las claves API (sk-...) no son compatibles. Por favor usa un token JWT en su lugar.",
+  "apiKeyNoLongerSupported": "Se cerró tu sesión porque las claves API ya no son compatibles. Por favor inicia sesión con un token JWT desde la configuración de OpenWebUI.",
   "tokenTooShort": "El token es demasiado corto",
   "signingIn": "Iniciando sesión...",
   "advancedSettings": "Configuración avanzada",
diff --git a/lib/l10n/app_fr.arb b/lib/l10n/app_fr.arb
index 5c11ee3..2063bed 100644
--- a/lib/l10n/app_fr.arb
+++ b/lib/l10n/app_fr.arb
@@ -230,6 +230,7 @@
   "enterToken": "Entrez votre jeton JWT",
   "tokenHint": "Obtenez le jeton JWT dans les paramètres d'OpenWebUI. Les clés API (sk-...) ne sont pas prises en charge pour le streaming.",
   "apiKeyNotSupported": "Les clés API (sk-...) ne sont pas prises en charge. Veuillez utiliser un jeton JWT à la place.",
+  "apiKeyNoLongerSupported": "Vous avez été déconnecté car les clés API ne sont plus prises en charge. Veuillez vous connecter avec un jeton JWT depuis les paramètres d'OpenWebUI.",
   "tokenTooShort": "Le jeton est trop court",
   "signingIn": "Connexion en cours...",
   "advancedSettings": "Paramètres avancés",
diff --git a/lib/l10n/app_it.arb b/lib/l10n/app_it.arb
index afb47fe..6d754fe 100644
--- a/lib/l10n/app_it.arb
+++ b/lib/l10n/app_it.arb
@@ -230,6 +230,7 @@
   "enterToken": "Inserisci il tuo token JWT",
   "tokenHint": "Ottieni il token JWT dalle impostazioni di OpenWebUI. Le chiavi API (sk-...) non sono supportate per lo streaming.",
   "apiKeyNotSupported": "Le chiavi API (sk-...) non sono supportate. Per favore usa un token JWT.",
+  "apiKeyNoLongerSupported": "Sei stato disconnesso perché le chiavi API non sono più supportate. Per favore accedi con un token JWT dalle impostazioni di OpenWebUI.",
   "tokenTooShort": "Il token è troppo corto",
   "signingIn": "Accesso in corso...",
   "advancedSettings": "Impostazioni avanzate",
diff --git a/lib/l10n/app_ko.arb b/lib/l10n/app_ko.arb
index 3b179f0..c0a5a53 100644
--- a/lib/l10n/app_ko.arb
+++ b/lib/l10n/app_ko.arb
@@ -340,6 +340,7 @@
   "enterToken": "JWT 토큰을 입력하세요",
   "tokenHint": "OpenWebUI 설정에서 JWT 토큰을 가져오세요. API 키(sk-...)는 스트리밍에 지원되지 않습니다.",
   "apiKeyNotSupported": "API 키(sk-...)는 지원되지 않습니다. JWT 토큰을 사용하세요.",
+  "apiKeyNoLongerSupported": "API 키가 더 이상 지원되지 않아 로그아웃되었습니다. OpenWebUI 설정에서 JWT 토큰으로 로그인하세요.",
   "tokenTooShort": "토큰이 너무 짧습니다",
   "signingIn": "로그인 중...",
   "advancedSettings": "고급 설정",
diff --git a/lib/l10n/app_nl.arb b/lib/l10n/app_nl.arb
index 2e68ccd..048151d 100644
--- a/lib/l10n/app_nl.arb
+++ b/lib/l10n/app_nl.arb
@@ -230,6 +230,7 @@
   "enterToken": "Voer je JWT-token in",
   "tokenHint": "Haal het JWT-token uit de OpenWebUI-instellingen. API-sleutels (sk-...) worden niet ondersteund voor streaming.",
   "apiKeyNotSupported": "API-sleutels (sk-...) worden niet ondersteund. Gebruik in plaats daarvan een JWT-token.",
+  "apiKeyNoLongerSupported": "Je bent uitgelogd omdat API-sleutels niet meer worden ondersteund. Log in met een JWT-token uit de OpenWebUI-instellingen.",
   "tokenTooShort": "Token is te kort",
   "signingIn": "Inloggen...",
   "advancedSettings": "Geavanceerde instellingen",
diff --git a/lib/l10n/app_ru.arb b/lib/l10n/app_ru.arb
index bd15449..66a963c 100644
--- a/lib/l10n/app_ru.arb
+++ b/lib/l10n/app_ru.arb
@@ -230,6 +230,7 @@
   "enterToken": "Введите ваш JWT-токен",
   "tokenHint": "Получите JWT-токен в настройках OpenWebUI. API-ключи (sk-...) не поддерживаются для потоковой передачи.",
   "apiKeyNotSupported": "API-ключи (sk-...) не поддерживаются. Пожалуйста, используйте JWT-токен.",
+  "apiKeyNoLongerSupported": "Вы были выведены из системы, так как API-ключи больше не поддерживаются. Пожалуйста, войдите с JWT-токеном из настроек OpenWebUI.",
   "tokenTooShort": "Токен слишком короткий",
   "signingIn": "Вход...",
   "advancedSettings": "Расширенные настройки",
diff --git a/lib/l10n/app_zh.arb b/lib/l10n/app_zh.arb
index b0d01ae..827d626 100644
--- a/lib/l10n/app_zh.arb
+++ b/lib/l10n/app_zh.arb
@@ -230,6 +230,7 @@
   "enterToken": "输入您的 JWT 令牌",
   "tokenHint": "从 OpenWebUI 设置获取 JWT 令牌。API 密钥 (sk-...) 不支持流式传输。",
   "apiKeyNotSupported": "不支持 API 密钥 (sk-...)。请改用 JWT 令牌。",
+  "apiKeyNoLongerSupported": "由于不再支持 API 密钥，您已被登出。请使用 OpenWebUI 设置中的 JWT 令牌登录。",
   "tokenTooShort": "令牌太短",
   "signingIn": "正在登录...",
   "advancedSettings": "高级设置",
diff --git a/lib/l10n/app_zh_Hant.arb b/lib/l10n/app_zh_Hant.arb
index 398f302..eae014e 100644
--- a/lib/l10n/app_zh_Hant.arb
+++ b/lib/l10n/app_zh_Hant.arb
@@ -230,6 +230,7 @@
   "enterToken": "輸入您的 JWT 令牌",
   "tokenHint": "從 OpenWebUI 設定取得 JWT 令牌。API 密鑰 (sk-...) 不支援串流。",
   "apiKeyNotSupported": "不支援 API 密鑰 (sk-...)。請改用 JWT 令牌。",
+  "apiKeyNoLongerSupported": "由於不再支援 API 密鑰，您已被登出。請使用 OpenWebUI 設定中的 JWT 令牌登入。",
   "tokenTooShort": "令牌太短",
   "signingIn": "正在登錄...",
   "advancedSettings": "高級設置",