Looping Login on Macbook

I have installed Tailscale 1.18.2 on my Macbook (Monterey 12.0.1).

When it loads up, I see a “thinking” tailscale icon in the upper right bar. Clicking the “Log in …” option in the dropdown does nothing.

I’ve tried reinstalling the application (completing all install steps except the KeyChain entry removal). Uninstalling Tailscale · Tailscale

This application has worked in the past and I’m not sure what triggered it to stop working:

  • I did upgrade operating systems
  • I did install antivirus software (sophos)

Let me know what other information I can provide to help troubleshoot.

The Sophos AV may be blocking the login pop-up. I would suggest that you try pausing protection and try logging in again.