diff --git a/core/src/types/message/messageEntity.ts b/core/src/types/message/messageEntity.ts
index f96919a8b..26bcad1a7 100644
--- a/core/src/types/message/messageEntity.ts
+++ b/core/src/types/message/messageEntity.ts
@@ -83,6 +83,8 @@ export enum MessageStatus {
 export enum ErrorCode {
   InvalidApiKey = 'invalid_api_key',
 
+  AuthenticationError = 'authentication_error',
+
   InsufficientQuota = 'insufficient_quota',
 
   InvalidRequestError = 'invalid_request_error',
diff --git a/web/containers/ErrorMessage/index.tsx b/web/containers/ErrorMessage/index.tsx
index 3979c3f4f..bcd056b93 100644
--- a/web/containers/ErrorMessage/index.tsx
+++ b/web/containers/ErrorMessage/index.tsx
@@ -41,12 +41,13 @@ const ErrorMessage = ({ message }: { message: ThreadMessage }) => {
       case ErrorCode.Unknown:
         return 'Apologies, something’s amiss!'
       case ErrorCode.InvalidApiKey:
+      case ErrorCode.AuthenticationError:
       case ErrorCode.InvalidRequestError:
         return (
           <span data-testid="invalid-API-key-error">
             Invalid API key. Please check your API key from{' '}
             <button
-              className="font-medium text-[hsla(var(--app-link))]"
+              className="font-medium text-[hsla(var(--app-link))] underline"
               onClick={() => {
                 setMainState(MainViewState.Settings)
 
@@ -102,7 +103,7 @@ const ErrorMessage = ({ message }: { message: ThreadMessage }) => {
           <p>
             Jan’s in beta. Access&nbsp;
             <span
-              className="cursor-pointer text-[hsla(var(--app-link))]"
+              className="cursor-pointer text-[hsla(var(--app-link))] underline"
               onClick={() => setModalTroubleShooting(true)}
             >
               troubleshooting assistance