Tailscale doesn't connect until someone logs into Windows

I installed Tailscale last night on a Windows Server vm. It worked fine until I had to restart the computer. When I did, I waited longer than I’m willing to admit for the computer to come back up. When it wasn’t reconnecting in the Tailscale admin console, I looked in my hypervisor to see that it was up and sitting on the lock screen. After some more testing I’m finding that Tailscale isn’t connecting until someone logs in which is not ideal for me. Is it possible to get Tailscale to connect as soon as the network goes up, before someone logs in using the (virtual) mouse and keyboard or RDPs in directly? I have a subnet router running as well so I can RDP in using it’s local subnet ip to get Tailscale running, then drop that connection and use a direct connection but that seems like a kludgy solution.


Is running unattended what you are looking for ?



Tailscale unattended on windows has been broken for quite some time. The near last comment on Windows Server Core cannot startup Tailscale · Issue #2137 · tailscale/tailscale · GitHub has some suggestions.

If the windows server has a GUI, login and configure unattended using the GUI tools only. It’s the CLI and remote scripts that is broken.