Otto says 'Failed to authenticate' or a 401 error: how to sign back in

You asked Otto something and instead of an answer you got an error like "Failed to authenticate. API Error: 401 OAuth access token has expired. Re-authenticate to continue." or "401 Invalid authentication credentials". This article explains what that message means and walks you through signing back in, step by step.

What this message means

The Claude sign-in on this computer expired. Otto runs on its own Claude AI account, and that sign-in is completely separate from your Gmail and Google connections - so reconnecting Google in the app does not help here. Asking Otto in chat cannot fix it either, because the chat itself needs that sign-in to work. The only fix is to sign back in, which takes about a minute.

How to sign back in

1. Above the message box, click Power view (it sits next to Chat).
2. In the top right of the terminal area, click the small Power-user view link. The app rechecks your sign-in.
3. One of two things happens next:
   • A screen titled "One quick sign-in" appears. Click Sign in now and finish signing in with your Claude account in the browser. If the browser shows a code at the end, copy it, paste it into Paste your sign-in code back in the app, and click Continue, then I'm signed in.
   • A terminal session opens instead. Type /login in the typing box and press Enter, then finish the browser sign-in the same way - and paste the code back into the app if the browser shows one.
4. Click back to Chat and ask Otto again. You are back in business.

Important: signing in at claude.ai alone is not enough

Signing in at claude.ai in your browser does not fix this on its own. The assistant on your computer keeps its own sign-in, so you need to go through the steps above so the app itself gets signed back in.

Coming soon: this fixes itself

An app update is on the way that recognises this exact error and routes you straight to the sign-in screen automatically, so you will not need to find your way through Power view at all.

Related articles

• Get Otto ready: the one-tap assistant setup screen
• Power view: the built-in terminal for power users

Still stuck? Submit a ticket from this help center and we will take it from there.