How can I ensure my Jellyfin container starts after a reboot with Docker Compose?

It looks like the main issue is that your Jellyfin service doesn't have a `restart` policy defined. You have `restart: always` set for your Tailscale container, but without it for Jellyfin, it won't automatically start after a reboot. Try adding `restart: always` to the Jellyfin section as well, and see if that fixes the problem! Some people also prefer `restart: unless-stopped` as it allows for safer maintenance reboots, but either should work fine here.

Just a heads up—Docker Compose doesn’t manage dependencies perfectly after a reboot. Having `depends_on` in your configuration might not be reliable in this case. You might want to explore creating a systemd service or startup script to handle starting your containers in the correct order after a system reboot. It may sound daunting, but it could really simplify things down the road.

You definitely want to ensure that both services have the same restart policy. Right now, Jellyfin lacks the `restart: always` setting, which means Docker won't start it automatically after a reboot. If adding that doesn't solve the issue, you might need to look into creating a startup script or using systemd to manage your containers. Docker Compose doesn’t automatically handle service dependencies during reboots, so a little extra setup might be necessary.