I have some of my Docker containers bind to Tailscale IPs on the host. Even though I edited the Docker service to depend on tailscaled.service and it starts about 10 seconds after it, every once in a while Tailscale interface won’t be ready by the time the containers try to spin up after a reboot.

Since restart policies do not apply to containers that has never started and ran at least for a while, Docker gives me no choice but to restart either those containers or the Docker daemon manually.

Is there a way to have Docker daemon try to restart containers even though they failed on the first try?

A restart policy only takes effect after a container starts successfully. In this case, starting successfully means that the container is up for at least 10 seconds and Docker has started monitoring it. This prevents a container which doesn’t start at all from going into a restart loop.

https://docs.docker.com/engine/containers/start-containers-automatically