I have been experimenting with headscale as well. I have it set up and everything works nicely but the Tailscale OSX client actually cannot automatically relogin.
Headscale has the preauthkey, it is still valid even but I need to do the tailscale up --login-server ... dance every time to get it connected.
Interesting. I've been running Headscale since the beginning of 2022, and haven't had any issues like this (MacOS Monterey). Have about 5-6 other MacOS users, and they haven't mentioned anything like this either.
I've probably logged in a grand total of two or three times (during initial testing in Jan). Everything "just works" for us.
Thank you, sounds like this will actually take care of it. I thought the /apple instructions were only for iOS since --login-server option was present on the binary already.
Headscale has the preauthkey, it is still valid even but I need to do the tailscale up --login-server ... dance every time to get it connected.
Not ideal.