Jellyfin on Docker hits a 443 port problem with Tailscale in the mix
A Debian server is set up with Tailscale installed first and Docker installed afterward. The planned setup is to reach Jellyfin through a purchased , route traffic through a cloud VPS, and use an . Everything except the VPS is meant to be bundled into Docker so backups and s are easier to manage.
Tailscale is also used so a laptop can SSH into the server for work. A basic Docker test with `docker run --rm hello-world` originally ran into a restricted 443 port connection, but it worked after applying `usermod` to the main non-Docker server user account. The same 443 connection error returned while trying to build a Jellyfin .
The practical question is whether Tailscale needs extra for builds, even before a is actually running.
Key points
- The server uses Debian, with Tailscale installed before Docker.
- The goal is to access Jellyfin through a , a cloud VPS, and an .
- The setup is meant to keep most services inside Docker for easier backup and imaging.
- A simple Docker test worked only after a `usermod` change to the main server user account.
- The same 443 port connection error appeared again while building a Jellyfin .