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Re:How our free plan stays free by therein on Wednesday March 16, 2022 @02:16PM (#30702147)
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.

Not ideal.

Re:How our free plan stays free by SparkyMcUnicorn on Wednesday March 16, 2022 @02:59PM (#30702602)
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.

Re:How our free plan stays free by kradalby on Wednesday March 16, 2022 @05:28PM (#30704333)
You can get macOS specific overrides that solve this by going to /apple on your headscale instance
Re:How our free plan stays free by therein on Wednesday March 16, 2022 @09:09PM (#30706299)
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.

> defaults write io.tailscale.ipn.macos ControlURL ...