Tailscale user:
My Team is using Tailscale extensively and we are happy with the performance, however there is one corner case that is a major blocker.
We have a number of macOS machines running unattended (pipelines/testing) and it seems that Tailscale service is not up until user logins into the session, therefore machine is not available on the VPN unless the user logs in.
Is there a solution for this?
Support:
The App Store version of Tailscale doesn’t support this (it’s a limitation of App Store apps, from what we understand).
But the open source version apparently supports the mode you want. Some people are working on that in https://github.com/tailscale/tailscale/issues/177 for Homebrew. But if you just want to build tailscaled and write a launchd config for it, it should work fine. We haven’t polished up that use case for macOS yet, but we might be able to help if you hit problems, though!