diff --git a/api/server/routes/oauth.js b/api/server/routes/oauth.js
index 046370798b..0a3ca9a249 100644
--- a/api/server/routes/oauth.js
+++ b/api/server/routes/oauth.js
@@ -22,6 +22,13 @@ const oauthHandler = async (req, res) => {
       return;
     }
     await setAuthTokens(req.user._id, res);
+    
+    // On successful login, let's clear any openid redirect flags
+    res.cookie('successful_login', 'true', { 
+      maxAge: 1000, // very short-lived, just for client-side detection
+      httpOnly: false // client needs to read this
+    });
+    
     res.redirect(domains.client);
   } catch (err) {
     logger.error('Error in setting authentication tokens:', err);
@@ -31,7 +38,9 @@ const oauthHandler = async (req, res) => {
 router.get('/error', (req, res) => {
   // A single error message is pushed by passport when authentication fails.
   logger.error('Error in OAuth authentication:', { message: req.session.messages.pop() });
-  res.redirect(`${domains.client}/login`);
+  
+  // Redirect to login page with auth_failed parameter to prevent infinite redirect loops
+  res.redirect(`${domains.client}/login?auth_failed=true`);
 });
 
 /**
diff --git a/client/src/components/Auth/Login.tsx b/client/src/components/Auth/Login.tsx
index db68bd7d42..311f40a9e2 100644
--- a/client/src/components/Auth/Login.tsx
+++ b/client/src/components/Auth/Login.tsx
@@ -3,7 +3,7 @@ import { useEffect, useRef } from 'react';
 import { useAuthContext } from '~/hooks/AuthContext';
 import type { TLoginLayoutContext } from '~/common';
 import { ErrorMessage } from '~/components/Auth/ErrorMessage';
-import { getLoginError } from '~/utils';
+import { getLoginError, shouldRedirectToOpenID, clearOpenIDRedirectFlag, getCookie } from '~/utils';
 import { useLocalize } from '~/hooks';
 import LoginForm from './LoginForm';
 
@@ -18,22 +18,40 @@ function Login() {
   // When enabled, users will be automatically redirected to the OpenID provider
   // without seeing the login form at all
   useEffect(() => {
-    // Simple check if redirect is needed and not yet attempted
+    // Check for URL parameters that indicate a failed auth attempt
+    const urlParams = new URLSearchParams(window.location.search);
+    const authFailed = urlParams.get('auth_failed') === 'true';
+
+    // Use the utility function to determine if we should redirect
     if (
-      !redirectAttemptedRef.current &&
-      startupConfig?.openidLoginEnabled &&
-      startupConfig?.openidAutoRedirect &&
-      startupConfig?.serverDomain
+      shouldRedirectToOpenID({
+        redirectAttempted: redirectAttemptedRef.current,
+        openidLoginEnabled: startupConfig?.openidLoginEnabled,
+        openidAutoRedirect: startupConfig?.openidAutoRedirect,
+        serverDomain: startupConfig?.serverDomain,
+        authFailed
+      })
     ) {
-      // Mark that we've attempted to redirect
+      // Mark that we've attempted to redirect in this component instance
       redirectAttemptedRef.current = true;
 
       // Log and redirect
       console.log('Auto-redirecting to OpenID provider...');
-      window.location.href = `${startupConfig.serverDomain}/oauth/openid`;
+      window.location.href = `${startupConfig?.serverDomain}/oauth/openid`;
     }
   }, [startupConfig]);
 
+  // Clear the redirect flag after successful login (when the cookie is present)
+  useEffect(() => {
+    const successfulLogin = getCookie('successful_login');
+    if (successfulLogin) {
+      // Clear the redirect flag in localStorage
+      clearOpenIDRedirectFlag();
+      
+      // Clear the cookie since we've processed it
+      document.cookie = 'successful_login=; Max-Age=0; path=/;';
+    }
+  }, []);
 
   return (
     <>
diff --git a/client/src/utils/localStorage.ts b/client/src/utils/localStorage.ts
index 3c44551b21..6975d2a9d6 100644
--- a/client/src/utils/localStorage.ts
+++ b/client/src/utils/localStorage.ts
@@ -1,5 +1,10 @@
 import { LocalStorageKeys, TConversation } from 'librechat-data-provider';
 
+// Key for tracking OpenID redirect attempts
+export const OPENID_REDIRECT_KEY = 'openid_redirect_attempted';
+// Cooldown period in milliseconds (5 minutes)
+export const OPENID_REDIRECT_COOLDOWN = 5 * 60 * 1000;
+
 export function getLocalStorageItems() {
   const items = {
     lastSelectedModel: localStorage.getItem(LocalStorageKeys.LAST_MODEL) ?? '',
@@ -24,6 +29,69 @@ export function getLocalStorageItems() {
   };
 }
 
+/**
+ * Handles the OpenID redirect logic to prevent infinite redirect loops
+ * @param conditions Object containing conditions that must be met for redirect
+ * @returns Boolean indicating whether to proceed with the redirect
+ */
+export function shouldRedirectToOpenID({
+  redirectAttempted,
+  openidLoginEnabled,
+  openidAutoRedirect,
+  serverDomain,
+  authFailed = false,
+}: {
+  redirectAttempted: boolean;
+  openidLoginEnabled?: boolean;
+  openidAutoRedirect?: boolean;
+  serverDomain?: string;
+  authFailed?: boolean;
+}): boolean {
+  // Get timestamp of last redirect attempt from localStorage
+  const lastRedirectAttempt = localStorage.getItem(OPENID_REDIRECT_KEY);
+  const currentTime = Date.now();
+  
+  // Only redirect if all conditions are met
+  if (
+    !redirectAttempted &&
+    openidLoginEnabled &&
+    openidAutoRedirect &&
+    serverDomain &&
+    !authFailed &&
+    (!lastRedirectAttempt || currentTime - parseInt(lastRedirectAttempt, 10) > OPENID_REDIRECT_COOLDOWN)
+  ) {
+    // Store the current timestamp in localStorage
+    localStorage.setItem(OPENID_REDIRECT_KEY, currentTime.toString());
+    return true;
+  }
+  
+  return false;
+}
+
+/**
+ * Clears the OpenID redirect tracking flag
+ */
+export function clearOpenIDRedirectFlag(): void {
+  localStorage.removeItem(OPENID_REDIRECT_KEY);
+}
+
+/**
+ * Gets a cookie value by name
+ * @param name The name of the cookie
+ * @returns The cookie value or null if not found
+ */
+export function getCookie(name: string): string | null {
+  const value = `; ${document.cookie}`;
+  const parts = value.split(`; ${name}=`);
+  if (parts.length === 2) {
+    const part = parts.pop();
+    if (part) {
+      return part.split(';').shift() || null;
+    }
+  }
+  return null;
+}
+
 export function clearLocalStorage(skipFirst?: boolean) {
   const keys = Object.keys(localStorage);
   keys.forEach((key) => {