Hi there,
I’d like to use Tailscale to be able to connect to a mac mini server I have. I need either Tailscale to startup when the system starts up or I need it to start up / connect when a system user logs in. We have a default login user setup on the server and we have Tailscale setup on that account, but when the system starts up Tailscale doesn’t connect. It only connects when we hit the “login” button. Is there a way to get Tailscale to automatically connect?
Thanks,
Joe Mifsud
Unfortunately this is a limitation of how macOS’s “Network Extension” API (which we use) works; it doesn’t take effect until our app is able to start, which only happens after system login and the tailscale GUI app starts.
Or are you seeing that Tailscale starts, the screen is unlocked, and tailscale itself needs you to login again?
I wish I had progressed that far! I don’t even have an app to load on the box.
The App Store won’t let me download / install Tailscale because the version of the O/S is not supported.
I found a GREAT thread about installing via HomeBrew, but that author hasn’t (to my knowledge) released the recipe. (Although it seems as if he’s close. If he needs guinea pigs, here I am! 
)
Work on a homebrew client is being tracked in https://github.com/tailscale/tailscale/issues/177, you can follow that issue for updates.
MacOS will not allow access to the NetworkExtension from a homebrew client, so an alternate interface mechanism will need to be developed for it. The alternate mechanism may also be able to support older versions of the MacOS, at this point that is not certain.
When I login as the the user I see the tailscale menu bar item but I do not see it auto connecting (the dots are not highlighted in the icon). I have to open the dropdown and click login. At that point nothing happens visually but after 5 - 10 seconds I see the dots in the menu bar icon light up and then I’m able to ping the machine. If I switch to the lock screen and login as another user Tailscale also seems to disconnect (I did not log out of the original user) because I’m no longer able to ping the machine.
FWIW, I saw that today too. We’ll investigate.