This is how to get the Windows client with headscale. I’m happy to finaly get it working.

Headscales docs are HERE, but I’m adding some more info since I wasn’t able to get it to work the first time

If you’ve already installed tailscale on the machine make sure to delete the C:\Users\<USERNAME>\AppData\Local\Tailscale directory

Download the Official Windows Client HERE and install it.

You can either do option A or B

Option A

Manually edit the registry

  • HKLM:\SOFTWARE\Tailscale IPN\UnattendedMode must be set to always as a string type, to allow Tailscale to run properly in the background
  • HKLM:\SOFTWARE\Tailscale IPN\LoginURL must be set to <YOUR HEADSCALE URL> as a string type, to ensure Tailscale contacts the correct control server.

Option B

I have created a reg file HERE that you can edit with Notepad++. Update https://URL_TO_HEADSCALE_SERVER with the URL to your headscale server

  1. Edit reg file from above

  2. Reboot machine

  3. Start tailscale client like normal

  4. Once the client starts it will say you have to auth

  5. Auth with server by clicking notification that says authentication is required

  6. This will open a URL with a command you have to run on your headscale server

  7. Run that command on your headscale server make sure to change the NAMESPACE to what namespace you want that device to be in

  8. Now you can go into windows settings and have headscale set to start at boot up