3 years in I finally ran into a #Tailscale issue that I couldn't resolve in 5 minutes: the macOS client got stuck in a bad state and literally every operation fails now including logging out and generating a bug report 
@msfjarvis does a reboot work? and while a bug report fails, can you click through and make a config report instead?
@erisa I did make a config report, will try a reboot now.
@msfjarvis if reboot doesn't work could you send the config report to support @ tailscale . com? I'll be able to see it then
@erisa a reboot sadly didn't solve the issue, I've sent an email. Thanks for taking a look!