by default, tailscaled service should start on boot on Raspbian Buster.
If it doesn’t happen in your case you, should check if it wasn’t failed on start:
sudo systemctl --failed
If you see tailscaled in the list you can check logs for why it wasn’t able to start normally:
They say that want=false is the problem, and is likely something going wrong when saving the /var/lib/tailscale/tailscaled.state file.
Support suggests it might be a filesystem options issue with the microSD card, but offer no suggestions on how to check that or address it.
I have 2 Raspberry Pis with different microSD cards, and I really don’t think it is a filesystem issue with the microSD card, since the problem is on both Pis and even though one is a fresh install, the other has had Tailscale on it for a long times, and both exhibit the issue.
Autostart used to work back in the Tailscale (1.5?) days, so I feel like perhaps something changed with Tailscale itself or something happened as part of the normal apt update/upgrade.
Just to be clear, I have vanilla Buster installs using Balenaetcher on macOS to the microSD card, followed by a fairly vanilla Pi-Hole install, and then Tailscale install. Support says they followed this process on their own Pi and had no issues with Tailscale starting on reboot.
I do not have any process I am aware of that clears out /etc.
Pretty vanilla install of Buster, Pi-Hole, and then Tailscale.
tailscaled.service was in /etc/systemd/system/multi-user.target.wants
Running systemctl enable --now tailscaled.service didn’t seem to help. Upon reboot, Tailscale still shows as stopped even though it was running just before rebooting.
cao-2000: we’ve already spent substantial time trying to reproduce the issue you’re reporting, on two different Raspberry Pi devices. We just don’t see this issue.