diff --git a/lib/features/auth/views/authentication_page.dart b/lib/features/auth/views/authentication_page.dart
index 00752e4..55b0f8a 100644
--- a/lib/features/auth/views/authentication_page.dart
+++ b/lib/features/auth/views/authentication_page.dart
@@ -399,7 +399,7 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
               icon: Platform.isIOS
                   ? CupertinoIcons.lock_shield
                   : Icons.vpn_key_outlined,
-              label: AppLocalizations.of(context)!.apiKey,
+              label: AppLocalizations.of(context)!.token,
               isSelected: _useApiKey,
               onTap: () => setState(() => _useApiKey = true),
             ),
@@ -480,24 +480,43 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
     );
   }
 
+  /// Validates that a token is a JWT and not an API key.
+  /// API keys (sk-, api-, key-) don't work with WebSocket authentication.
+  String? _validateJwtToken(String? value) {
+    if (value == null || value.isEmpty) {
+      return AppLocalizations.of(context)!.validationMissingRequired;
+    }
+
+    final trimmed = value.trim();
+    final lowerTrimmed = trimmed.toLowerCase();
+
+    // Reject API keys - they don't work with socket authentication
+    // Case-insensitive check to catch SK-, API-, KEY- variants
+    if (lowerTrimmed.startsWith('sk-') ||
+        lowerTrimmed.startsWith('api-') ||
+        lowerTrimmed.startsWith('key-')) {
+      return AppLocalizations.of(context)!.apiKeyNotSupported;
+    }
+
+    // Check minimum length
+    if (trimmed.length < 10) {
+      return AppLocalizations.of(context)!.tokenTooShort;
+    }
+
+    return null;
+  }
+
   Widget _buildApiKeyForm() {
     return Column(
       key: const ValueKey('api_key_form'),
       children: [
         AccessibleFormField(
-          label: AppLocalizations.of(context)!.apiKey,
-          hint: 'sk-...',
+          label: AppLocalizations.of(context)!.token,
+          hint: 'eyJ...',
           controller: _apiKeyController,
-          validator: InputValidationService.combine([
-            InputValidationService.validateRequired,
-            (value) => InputValidationService.validateMinLength(
-              value,
-              10,
-              fieldName: AppLocalizations.of(context)!.apiKey,
-            ),
-          ]),
+          validator: _validateJwtToken,
           obscureText: _obscurePassword,
-          semanticLabel: AppLocalizations.of(context)!.enterApiKey,
+          semanticLabel: AppLocalizations.of(context)!.enterToken,
           prefixIcon: Icon(
             Platform.isIOS
                 ? CupertinoIcons.lock_shield
@@ -520,6 +539,13 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
           isRequired: true,
           autofillHints: const [AutofillHints.password],
         ),
+        const SizedBox(height: Spacing.sm),
+        Text(
+          AppLocalizations.of(context)!.tokenHint,
+          style: context.conduitTheme.bodySmall?.copyWith(
+            color: context.conduitTheme.textSecondary,
+          ),
+        ),
       ],
     );
   }
@@ -591,7 +617,7 @@ class _AuthenticationPageState extends ConsumerState<AuthenticationPage> {
         text: _isSigningIn
             ? AppLocalizations.of(context)!.signingIn
             : _useApiKey
-            ? AppLocalizations.of(context)!.signInWithApiKey
+            ? AppLocalizations.of(context)!.signInWithToken
             : AppLocalizations.of(context)!.signIn,
         icon: _isSigningIn
             ? null
diff --git a/lib/l10n/app_de.arb b/lib/l10n/app_de.arb
index b74147c..1df3ba1 100644
--- a/lib/l10n/app_de.arb
+++ b/lib/l10n/app_de.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Gib deine Anmeldedaten ein, um auf deine KI-Unterhaltungen zuzugreifen",
   "credentials": "Zugangsdaten",
   "apiKey": "API-Schlüssel",
+  "token": "Token",
   "usernameOrEmail": "Benutzername oder E‑Mail",
   "password": "Passwort",
   "signInWithApiKey": "Mit API-Schlüssel anmelden",
+  "signInWithToken": "Mit Token anmelden",
   "connectToServer": "Mit Server verbinden",
   "enterServerAddress": "Gib die Adresse deines Open-WebUI-Servers ein, um zu beginnen",
   "serverUrl": "Server-URL",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Gib deinen Benutzernamen oder deine E‑Mail ein",
   "passwordHint": "Gib dein Passwort ein",
   "enterApiKey": "Gib deinen API-Schlüssel ein",
+  "enterToken": "Gib dein JWT-Token ein",
+  "tokenHint": "Verwende ein JWT-Token aus Browser-Cookies oder API-Login. API-Schlüssel (sk-...) werden für Streaming nicht unterstützt.",
+  "apiKeyNotSupported": "API-Schlüssel (sk-...) werden nicht unterstützt. Bitte verwende stattdessen ein JWT-Token.",
+  "tokenTooShort": "Token ist zu kurz",
   "signingIn": "Anmeldung läuft...",
   "advancedSettings": "Erweiterte Einstellungen",
   "customHeaders": "Benutzerdefinierte Header",
diff --git a/lib/l10n/app_en.arb b/lib/l10n/app_en.arb
index 0de9784..108e8de 100644
--- a/lib/l10n/app_en.arb
+++ b/lib/l10n/app_en.arb
@@ -216,6 +216,10 @@
   "@apiKey": {
     "description": "Label for API key input field."
   },
+  "token": "Token",
+  "@token": {
+    "description": "Label for JWT token input field."
+  },
   "usernameOrEmail": "Username or Email",
   "@usernameOrEmail": {
     "description": "Label for username/email input field."
@@ -228,6 +232,10 @@
   "@signInWithApiKey": {
     "description": "Alternative sign-in method using an API key."
   },
+  "signInWithToken": "Sign in with Token",
+  "@signInWithToken": {
+    "description": "Alternative sign-in method using a JWT token."
+  },
   "connectToServer": "Connect to Server",
   "@connectToServer": {
     "description": "Call-to-action button for server connection."
@@ -1004,6 +1012,22 @@
   "@enterApiKey": {
     "description": "Hint text for API key input."
   },
+  "enterToken": "Enter your JWT token",
+  "@enterToken": {
+    "description": "Hint text for JWT token input."
+  },
+  "tokenHint": "Use a JWT token from browser cookies or API login. API keys (sk-...) are not supported for streaming.",
+  "@tokenHint": {
+    "description": "Help text explaining what type of token to use."
+  },
+  "apiKeyNotSupported": "API keys (sk-...) are not supported. Please use a JWT token instead.",
+  "@apiKeyNotSupported": {
+    "description": "Error message when user tries to use an API key instead of JWT token."
+  },
+  "tokenTooShort": "Token is too short",
+  "@tokenTooShort": {
+    "description": "Error message when token is too short."
+  },
   "signingIn": "Signing in...",
   "@signingIn": {
     "description": "Status message shown while signing in."
diff --git a/lib/l10n/app_es.arb b/lib/l10n/app_es.arb
index d7f2474..df054c1 100644
--- a/lib/l10n/app_es.arb
+++ b/lib/l10n/app_es.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Ingresa tus credenciales para acceder a tus conversaciones de IA",
   "credentials": "Credenciales",
   "apiKey": "Clave API",
+  "token": "Token",
   "usernameOrEmail": "Usuario o correo electrónico",
   "password": "Contraseña",
   "signInWithApiKey": "Iniciar sesión con clave API",
+  "signInWithToken": "Iniciar sesión con token",
   "connectToServer": "Conectar al servidor",
   "enterServerAddress": "Ingresa la dirección de tu servidor Open-WebUI para comenzar",
   "serverUrl": "URL del servidor",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Ingresa tu usuario o correo electrónico",
   "passwordHint": "Ingresa tu contraseña",
   "enterApiKey": "Ingresa tu clave API",
+  "enterToken": "Ingresa tu token JWT",
+  "tokenHint": "Usa un token JWT de las cookies del navegador o del inicio de sesión API. 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.",
+  "tokenTooShort": "El token es demasiado corto",
   "signingIn": "Iniciando sesión...",
   "advancedSettings": "Configuración avanzada",
   "customHeaders": "Encabezados personalizados",
diff --git a/lib/l10n/app_fr.arb b/lib/l10n/app_fr.arb
index d3f8cee..c370ec0 100644
--- a/lib/l10n/app_fr.arb
+++ b/lib/l10n/app_fr.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Entrez vos identifiants pour accéder à vos conversations IA",
   "credentials": "Identifiants",
   "apiKey": "Clé API",
+  "token": "Jeton",
   "usernameOrEmail": "Nom d'utilisateur ou e‑mail",
   "password": "Mot de passe",
   "signInWithApiKey": "Se connecter avec une clé API",
+  "signInWithToken": "Se connecter avec un jeton",
   "connectToServer": "Se connecter au serveur",
   "enterServerAddress": "Saisissez l'adresse de votre serveur Open-WebUI pour commencer",
   "serverUrl": "URL du serveur",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Entrez votre nom d'utilisateur ou e‑mail",
   "passwordHint": "Entrez votre mot de passe",
   "enterApiKey": "Entrez votre clé API",
+  "enterToken": "Entrez votre jeton JWT",
+  "tokenHint": "Utilisez un jeton JWT des cookies du navigateur ou de la connexion API. 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.",
+  "tokenTooShort": "Le jeton est trop court",
   "signingIn": "Connexion en cours...",
   "advancedSettings": "Paramètres avancés",
   "customHeaders": "En-têtes personnalisés",
diff --git a/lib/l10n/app_it.arb b/lib/l10n/app_it.arb
index f8bde04..aa5f082 100644
--- a/lib/l10n/app_it.arb
+++ b/lib/l10n/app_it.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Inserisci le credenziali per accedere alle conversazioni IA",
   "credentials": "Credenziali",
   "apiKey": "Chiave API",
+  "token": "Token",
   "usernameOrEmail": "Username o e‑mail",
   "password": "Password",
   "signInWithApiKey": "Accedi con chiave API",
+  "signInWithToken": "Accedi con token",
   "connectToServer": "Connetti al server",
   "enterServerAddress": "Inserisci l'indirizzo del server Open-WebUI per iniziare",
   "serverUrl": "URL del server",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Inserisci il tuo username o e‑mail",
   "passwordHint": "Inserisci la password",
   "enterApiKey": "Inserisci la tua chiave API",
+  "enterToken": "Inserisci il tuo token JWT",
+  "tokenHint": "Usa un token JWT dai cookie del browser o dal login API. Le chiavi API (sk-...) non sono supportate per lo streaming.",
+  "apiKeyNotSupported": "Le chiavi API (sk-...) non sono supportate. Per favore usa un token JWT.",
+  "tokenTooShort": "Il token è troppo corto",
   "signingIn": "Accesso in corso...",
   "advancedSettings": "Impostazioni avanzate",
   "customHeaders": "Header personalizzati",
diff --git a/lib/l10n/app_ko.arb b/lib/l10n/app_ko.arb
index 93f7199..881fe3f 100644
--- a/lib/l10n/app_ko.arb
+++ b/lib/l10n/app_ko.arb
@@ -87,9 +87,11 @@
   "enterCredentials": "AI 대화에 액세스하려면 자격 증명을 입력하세요",
   "credentials": "자격 증명",
   "apiKey": "API 키",
+  "token": "토큰",
   "usernameOrEmail": "사용자 이름 또는 이메일",
   "password": "비밀번호",
   "signInWithApiKey": "API 키로 로그인",
+  "signInWithToken": "토큰으로 로그인",
   "connectToServer": "서버 연결",
   "enterServerAddress": "시작하려면 Open-WebUI 서버 주소를 입력하세요",
   "serverUrl": "서버 URL",
@@ -335,6 +337,10 @@
   "usernameOrEmailHint": "사용자 이름 또는 이메일을 입력하세요",
   "passwordHint": "비밀번호를 입력하세요",
   "enterApiKey": "API 키를 입력하세요",
+  "enterToken": "JWT 토큰을 입력하세요",
+  "tokenHint": "브라우저 쿠키 또는 API 로그인에서 JWT 토큰을 사용하세요. API 키(sk-...)는 스트리밍에 지원되지 않습니다.",
+  "apiKeyNotSupported": "API 키(sk-...)는 지원되지 않습니다. JWT 토큰을 사용하세요.",
+  "tokenTooShort": "토큰이 너무 짧습니다",
   "signingIn": "로그인 중...",
   "advancedSettings": "고급 설정",
   "customHeaders": "사용자 정의 헤더",
diff --git a/lib/l10n/app_nl.arb b/lib/l10n/app_nl.arb
index b706083..c8e2534 100644
--- a/lib/l10n/app_nl.arb
+++ b/lib/l10n/app_nl.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Voer je inloggegevens in om toegang te krijgen tot je AI-gesprekken",
   "credentials": "Inloggegevens",
   "apiKey": "API-sleutel",
+  "token": "Token",
   "usernameOrEmail": "Gebruikersnaam of e-mail",
   "password": "Wachtwoord",
   "signInWithApiKey": "Inloggen met API-sleutel",
+  "signInWithToken": "Inloggen met token",
   "connectToServer": "Verbinden met server",
   "enterServerAddress": "Voer je Open-WebUI serveradres in om te beginnen",
   "serverUrl": "Server-URL",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Voer je gebruikersnaam of e-mail in",
   "passwordHint": "Voer je wachtwoord in",
   "enterApiKey": "Voer je API-sleutel in",
+  "enterToken": "Voer je JWT-token in",
+  "tokenHint": "Gebruik een JWT-token van browsercookies of API-login. API-sleutels (sk-...) worden niet ondersteund voor streaming.",
+  "apiKeyNotSupported": "API-sleutels (sk-...) worden niet ondersteund. Gebruik in plaats daarvan een JWT-token.",
+  "tokenTooShort": "Token is te kort",
   "signingIn": "Inloggen...",
   "advancedSettings": "Geavanceerde instellingen",
   "customHeaders": "Aangepaste headers",
diff --git a/lib/l10n/app_ru.arb b/lib/l10n/app_ru.arb
index 41cd196..b522c67 100644
--- a/lib/l10n/app_ru.arb
+++ b/lib/l10n/app_ru.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "Введите свои учетные данные для доступа к вашим разговорам с ИИ",
   "credentials": "Учетные данные",
   "apiKey": "API-ключ",
+  "token": "Токен",
   "usernameOrEmail": "Имя пользователя или email",
   "password": "Пароль",
   "signInWithApiKey": "Войти с помощью API-ключа",
+  "signInWithToken": "Войти с помощью токена",
   "connectToServer": "Подключиться к серверу",
   "enterServerAddress": "Введите адрес вашего сервера Open-WebUI для начала",
   "serverUrl": "URL сервера",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "Введите ваше имя пользователя или email",
   "passwordHint": "Введите ваш пароль",
   "enterApiKey": "Введите ваш API-ключ",
+  "enterToken": "Введите ваш JWT-токен",
+  "tokenHint": "Используйте JWT-токен из cookies браузера или входа через API. API-ключи (sk-...) не поддерживаются для потоковой передачи.",
+  "apiKeyNotSupported": "API-ключи (sk-...) не поддерживаются. Пожалуйста, используйте JWT-токен.",
+  "tokenTooShort": "Токен слишком короткий",
   "signingIn": "Вход...",
   "advancedSettings": "Расширенные настройки",
   "customHeaders": "Пользовательские заголовки",
diff --git a/lib/l10n/app_zh.arb b/lib/l10n/app_zh.arb
index 4148d33..69f9760 100644
--- a/lib/l10n/app_zh.arb
+++ b/lib/l10n/app_zh.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "输入您的凭据以访问您的 AI 对话",
   "credentials": "凭据",
   "apiKey": "API 密钥",
+  "token": "令牌",
   "usernameOrEmail": "用户名或电子邮件",
   "password": "密码",
   "signInWithApiKey": "使用 API 密钥登录",
+  "signInWithToken": "使用令牌登录",
   "connectToServer": "连接到服务器",
   "enterServerAddress": "输入您的 Open-WebUI 服务器地址以开始",
   "serverUrl": "服务器 URL",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "输入您的用户名或电子邮件",
   "passwordHint": "输入您的密码",
   "enterApiKey": "输入您的 API 密钥",
+  "enterToken": "输入您的 JWT 令牌",
+  "tokenHint": "请使用浏览器 cookie 或 API 登录中的 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。",
+  "tokenTooShort": "令牌太短",
   "signingIn": "正在登录...",
   "advancedSettings": "高级设置",
   "customHeaders": "自定义标头",
diff --git a/lib/l10n/app_zh_Hant.arb b/lib/l10n/app_zh_Hant.arb
index 9b8433c..30ce779 100644
--- a/lib/l10n/app_zh_Hant.arb
+++ b/lib/l10n/app_zh_Hant.arb
@@ -46,9 +46,11 @@
   "enterCredentials": "輸入您的憑據以訪問您的 AI 對話",
   "credentials": "憑據",
   "apiKey": "API 密鑰",
+  "token": "令牌",
   "usernameOrEmail": "用戶名或電子郵件",
   "password": "密碼",
   "signInWithApiKey": "使用 API 密鑰登錄",
+  "signInWithToken": "使用令牌登錄",
   "connectToServer": "連接到服務器",
   "enterServerAddress": "輸入您的 Open-WebUI 服務器地址以開始",
   "serverUrl": "服務器 URL",
@@ -225,6 +227,10 @@
   "usernameOrEmailHint": "輸入您的用戶名或電子郵件",
   "passwordHint": "輸入您的密碼",
   "enterApiKey": "輸入您的 API 密鑰",
+  "enterToken": "輸入您的 JWT 令牌",
+  "tokenHint": "請使用瀏覽器 cookie 或 API 登入中的 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。",
+  "tokenTooShort": "令牌太短",
   "signingIn": "正在登錄...",
   "advancedSettings": "高級設置",
   "customHeaders": "自定義標頭",