Tailscale not showing in menu bar after macos 12.1 upgrade

Tailscale version: 1.20.1
Your operating system & version: macos 12.1

A user on my tailscale network upgraded to macos 12.1 and reported that they could no longer start tailscale. They uninstalled and reinstalled from the app store, but still every time they launched tailscale nothing would happen. I double checked that they were not connected, manually connected them by running /Applications/Tailscale.app/Contents/MacOS/Tailscale up from the terminal, and then double checked that they were now connected.

So it seems as if tailscaled is working just fine, but that the macos menubar app is failing to launch or at least appear.

Any guidance would be appreciated, and if this isn’t the place for this I can move this. As it seems to be an issue with only the closed source macos bits, a GitHub issue didn’t seem appropriate.

A couple things to check:

  • Does systemextensionctl list show more than one Tailscale extension? If so, rebooting the Mac is likely to help.
  • Does systemextensionctl list show some other product’s extension? Conflicts are possible, though we’d expect the 1.18 release to have had the same conflicts.
  • /Applications/Utilities/Console.app and search for “IPN” and “tailscale” may turn up errors or crashes from the front end while it is trying to start.