diff --git a/application/app.py b/application/app.py
index ddac00b0..7ca0ac2b 100644
--- a/application/app.py
+++ b/application/app.py
@@ -1,10 +1,12 @@
+import os
 import platform
+import uuid
 
 import dotenv
 from flask import Flask, jsonify, redirect, request
 from jose import jwt
 
-from application.auth import get_or_create_user_id, handle_auth
+from application.auth import handle_auth
 
 from application.core.logging_config import setup_logging
 
@@ -38,10 +40,22 @@ app.config.update(
 celery.config_from_object("application.celeryconfig")
 api.init_app(app)
 
+if settings.AUTH_TYPE in ("simple_jwt", "session_jwt") and not settings.JWT_SECRET_KEY:
+    key_file = ".jwt_secret_key"
+    try:
+        with open(key_file, "r") as f:
+            settings.JWT_SECRET_KEY = f.read().strip()
+    except FileNotFoundError:
+        new_key = os.urandom(32).hex()
+        with open(key_file, "w") as f:
+            f.write(new_key)
+        settings.JWT_SECRET_KEY = new_key
+    except Exception as e:
+        raise RuntimeError(f"Failed to setup JWT_SECRET_KEY: {e}")
+
 SIMPLE_JWT_TOKEN = None
 if settings.AUTH_TYPE == "simple_jwt":
-    user_id = get_or_create_user_id()
-    payload = {"sub": user_id}
+    payload = {"sub": "local"}
     SIMPLE_JWT_TOKEN = jwt.encode(payload, settings.JWT_SECRET_KEY, algorithm="HS256")
     print(f"Generated Simple JWT Token: {SIMPLE_JWT_TOKEN}")
 
@@ -54,13 +68,33 @@ def home():
         return "Welcome to DocsGPT Backend!"
 
 
+@app.route("/api/config")
+def get_config():
+    response = {
+        "auth_type": settings.AUTH_TYPE,
+        "requires_auth": settings.AUTH_TYPE in ["simple_jwt", "session_jwt"],
+    }
+    return jsonify(response)
+
+
+@app.route("/api/generate_token")
+def generate_token():
+    if settings.AUTH_TYPE == "session_jwt":
+        new_user_id = str(uuid.uuid4())
+        token = jwt.encode(
+            {"sub": new_user_id}, settings.JWT_SECRET_KEY, algorithm="HS256"
+        )
+        return jsonify({"token": token})
+    return jsonify({"error": "Token generation not allowed in current auth mode"}), 400
+
+
 @app.before_request
 def authenticate_request():
     if request.method == "OPTIONS":
         return "", 200
 
     decoded_token = handle_auth(request)
-    if "message" in decoded_token:
+    if not decoded_token:
         request.decoded_token = None
     elif "error" in decoded_token:
         return jsonify(decoded_token), 401
diff --git a/application/auth.py b/application/auth.py
index be2501b0..78926c45 100644
--- a/application/auth.py
+++ b/application/auth.py
@@ -1,15 +1,13 @@
-import uuid
-
 from jose import jwt
 
 from application.core.settings import settings
 
 
 def handle_auth(request, data={}):
-    if settings.AUTH_TYPE == "simple_jwt":
+    if settings.AUTH_TYPE in ["simple_jwt", "session_jwt"]:
         jwt_token = request.headers.get("Authorization")
         if not jwt_token:
-            return {"message": "Missing Authorization header"}
+            return None
 
         jwt_token = jwt_token.replace("Bearer ", "")
 
@@ -22,18 +20,9 @@ def handle_auth(request, data={}):
             )
             return decoded_token
         except Exception as e:
-            return {"message": f"Authentication error: {str(e)}"}
+            return {
+                "message": f"Authentication error: {str(e)}",
+                "error": "invalid_token",
+            }
     else:
         return {"sub": "local"}
-
-
-def get_or_create_user_id():
-    try:
-        with open(settings.USER_ID_FILE, "r") as f:
-            user_id = f.read().strip()
-            return user_id
-    except FileNotFoundError:
-        user_id = str(uuid.uuid4())
-        with open(settings.USER_ID_FILE, "w") as f:
-            f.write(user_id)
-        return user_id
diff --git a/application/core/settings.py b/application/core/settings.py
index a757a7f3..2a78b3a0 100644
--- a/application/core/settings.py
+++ b/application/core/settings.py
@@ -100,7 +100,6 @@ class Settings(BaseSettings):
     FLASK_DEBUG_MODE: bool = False
 
     JWT_SECRET_KEY: str = ""
-    USER_ID_FILE: str = os.path.join(current_dir, "user_id.txt")
 
 
 path = Path(__file__).parent.parent.absolute()
diff --git a/frontend/src/App.tsx b/frontend/src/App.tsx
index ba0a4bd7..64c4c486 100644
--- a/frontend/src/App.tsx
+++ b/frontend/src/App.tsx
@@ -1,15 +1,30 @@
-import { Routes, Route } from 'react-router-dom';
-import Navigation from './Navigation';
-import Conversation from './conversation/Conversation';
-import About from './About';
-import PageNotFound from './PageNotFound';
-import { useMediaQuery } from './hooks';
-import { useState } from 'react';
-import Setting from './settings';
 import './locale/i18n';
-import { Outlet } from 'react-router-dom';
+
+import { useState } from 'react';
+import { Outlet, Route, Routes } from 'react-router-dom';
+
+import About from './About';
+import Spinner from './components/Spinner';
+import Conversation from './conversation/Conversation';
 import { SharedConversation } from './conversation/SharedConversation';
-import { useDarkTheme } from './hooks';
+import { useDarkTheme, useMediaQuery } from './hooks';
+import useTokenAuth from './hooks/useTokenAuth';
+import Navigation from './Navigation';
+import PageNotFound from './PageNotFound';
+import Setting from './settings';
+
+function AuthWrapper({ children }: { children: React.ReactNode }) {
+  const { isAuthLoading } = useTokenAuth();
+
+  if (isAuthLoading) {
+    return (
+      <div className="h-screen flex items-center justify-center">
+        <Spinner />
+      </div>
+    );
+  }
+  return <>{children}</>;
+}
 
 function MainLayout() {
   const { isMobile } = useMediaQuery();
@@ -39,7 +54,13 @@ export default function App() {
   return (
     <div className="h-full relative overflow-auto">
       <Routes>
-        <Route element={<MainLayout />}>
+        <Route
+          element={
+            <AuthWrapper>
+              <MainLayout />
+            </AuthWrapper>
+          }
+        >
           <Route index element={<Conversation />} />
           <Route path="/about" element={<About />} />
           <Route path="/settings" element={<Setting />} />
diff --git a/frontend/src/Navigation.tsx b/frontend/src/Navigation.tsx
index ad30228b..c0fb8231 100644
--- a/frontend/src/Navigation.tsx
+++ b/frontend/src/Navigation.tsx
@@ -28,6 +28,7 @@ import {
 import ConversationTile from './conversation/ConversationTile';
 import { useDarkTheme, useMediaQuery } from './hooks';
 import useDefaultDocument from './hooks/useDefaultDocument';
+import useTokenAuth from './hooks/useTokenAuth';
 import DeleteConvModal from './modals/DeleteConvModal';
 import JWTModal from './modals/JWTModal';
 import { ActiveState, Doc } from './models/misc';
@@ -72,10 +73,10 @@ export default function Navigation({ navOpen, setNavOpen }: NavigationProps) {
   const { t } = useTranslation();
   const isApiKeySet = useSelector(selectApiKeyStatus);
 
+  const { showTokenModal, handleTokenSubmit } = useTokenAuth();
+
   const [uploadModalState, setUploadModalState] =
     useState<ActiveState>('INACTIVE');
-  const [authKeyModalState, setAuthKeyModalState] =
-    useState<ActiveState>('INACTIVE');
 
   const navRef = useRef(null);
 
@@ -204,15 +205,7 @@ export default function Navigation({ navOpen, setNavOpen }: NavigationProps) {
     setNavOpen(!isMobile);
   }, [isMobile]);
 
-  useEffect(() => {
-    const authToken = localStorage.getItem('authToken');
-    if (!authToken) {
-      setAuthKeyModalState('ACTIVE');
-    }
-  }, []);
-
   useDefaultDocument();
-
   return (
     <>
       {!navOpen && (
@@ -485,8 +478,8 @@ export default function Navigation({ navOpen, setNavOpen }: NavigationProps) {
         ></Upload>
       )}
       <JWTModal
-        modalState={authKeyModalState}
-        setModalState={setAuthKeyModalState}
+        modalState={showTokenModal ? 'ACTIVE' : 'INACTIVE'}
+        handleTokenSubmit={handleTokenSubmit}
       />
     </>
   );
diff --git a/frontend/src/api/endpoints.ts b/frontend/src/api/endpoints.ts
index 9bf659de..0d574f89 100644
--- a/frontend/src/api/endpoints.ts
+++ b/frontend/src/api/endpoints.ts
@@ -1,5 +1,7 @@
 const endpoints = {
   USER: {
+    CONFIG: '/api/config',
+    NEW_TOKEN: '/api/generate_token',
     DOCS: '/api/sources',
     DOCS_CHECK: '/api/docs_check',
     DOCS_PAGINATED: '/api/sources/paginated',
diff --git a/frontend/src/api/services/userService.ts b/frontend/src/api/services/userService.ts
index fbaa06ba..13083677 100644
--- a/frontend/src/api/services/userService.ts
+++ b/frontend/src/api/services/userService.ts
@@ -2,6 +2,9 @@ import apiClient from '../client';
 import endpoints from '../endpoints';
 
 const userService = {
+  getConfig: (): Promise<any> => apiClient.get(endpoints.USER.CONFIG, null),
+  getNewToken: (): Promise<any> =>
+    apiClient.get(endpoints.USER.NEW_TOKEN, null),
   getDocs: (token: string | null): Promise<any> =>
     apiClient.get(`${endpoints.USER.DOCS}`, token),
   getDocsWithPagination: (query: string, token: string | null): Promise<any> =>
diff --git a/frontend/src/hooks/useTokenAuth.ts b/frontend/src/hooks/useTokenAuth.ts
new file mode 100644
index 00000000..8f408600
--- /dev/null
+++ b/frontend/src/hooks/useTokenAuth.ts
@@ -0,0 +1,55 @@
+import { useEffect, useRef, useState } from 'react';
+import { useDispatch, useSelector } from 'react-redux';
+
+import userService from '../api/services/userService';
+import { selectToken, setToken } from '../preferences/preferenceSlice';
+
+export default function useAuth() {
+  const dispatch = useDispatch();
+  const token = useSelector(selectToken);
+  const [authType, setAuthType] = useState(null);
+  const [showTokenModal, setShowTokenModal] = useState(false);
+  const [isAuthLoading, setIsAuthLoading] = useState(true);
+  const isGeneratingToken = useRef(false);
+
+  const generateNewToken = async () => {
+    if (isGeneratingToken.current) return;
+    isGeneratingToken.current = true;
+    const response = await userService.getNewToken();
+    const { token: newToken } = await response.json();
+    localStorage.setItem('authToken', newToken);
+    dispatch(setToken(newToken));
+    setIsAuthLoading(false);
+    return newToken;
+  };
+
+  useEffect(() => {
+    const initializeAuth = async () => {
+      try {
+        const configRes = await userService.getConfig();
+        const config = await configRes.json();
+        setAuthType(config.auth_type);
+
+        if (config.auth_type === 'session_jwt' && !token) {
+          await generateNewToken();
+        } else if (config.auth_type === 'simple_jwt' && !token) {
+          setShowTokenModal(true);
+          setIsAuthLoading(false);
+        } else {
+          setIsAuthLoading(false);
+        }
+      } catch (error) {
+        console.error('Auth initialization failed:', error);
+        setIsAuthLoading(false);
+      }
+    };
+    initializeAuth();
+  }, []);
+
+  const handleTokenSubmit = (enteredToken: string) => {
+    localStorage.setItem('authToken', enteredToken);
+    dispatch(setToken(enteredToken));
+    setShowTokenModal(false);
+  };
+  return { authType, showTokenModal, isAuthLoading, token, handleTokenSubmit };
+}
diff --git a/frontend/src/modals/JWTModal.tsx b/frontend/src/modals/JWTModal.tsx
index 90a13254..1cab145e 100644
--- a/frontend/src/modals/JWTModal.tsx
+++ b/frontend/src/modals/JWTModal.tsx
@@ -3,30 +3,23 @@ import { useDispatch } from 'react-redux';
 
 import Input from '../components/Input';
 import { ActiveState } from '../models/misc';
-import { setToken } from '../preferences/preferenceSlice';
 import WrapperModal from './WrapperModal';
 
 type JWTModalProps = {
   modalState: ActiveState;
-  setModalState: (state: ActiveState) => void;
+  handleTokenSubmit: (enteredToken: string) => void;
 };
 
-export default function JWTModal({ modalState, setModalState }: JWTModalProps) {
-  const dispatch = useDispatch();
+export default function JWTModal({
+  modalState,
+  handleTokenSubmit,
+}: JWTModalProps) {
   const [jwtToken, setJwtToken] = useState<string>('');
 
-  const handleSaveToken = () => {
-    if (jwtToken) {
-      localStorage.setItem('authToken', jwtToken);
-      dispatch(setToken(jwtToken));
-      setModalState('INACTIVE');
-    }
-  };
-
   if (modalState !== 'ACTIVE') return null;
 
   return (
-    <WrapperModal close={() => setModalState('INACTIVE')} className="p-4">
+    <WrapperModal className="p-4" isPerformingTask={true} close={() => {}}>
       <div className="mb-6">
         <span className="text-lg text-jet dark:text-bright-gray">
           Add JWT Token
@@ -44,7 +37,7 @@ export default function JWTModal({ modalState, setModalState }: JWTModalProps) {
       </div>
       <button
         disabled={jwtToken.length === 0}
-        onClick={handleSaveToken}
+        onClick={handleTokenSubmit.bind(null, jwtToken)}
         className="float-right mt-4 rounded-full bg-purple-30 px-5 py-2 text-sm text-white hover:bg-[#6F3FD1] disabled:opacity-50"
       >
         Save Token