

You have a lot going on there all at once that could be contributing to the whole thing failing.
If it were me, I would try to get caddy working independently of everything else first, since it was your original problem, then layer in the other containers one by one in case you’ve got configuration problems in them too.
Caddy by itself is super easy to verify with something like a browse directive pointed at an empty directory.
Then add your tailscale container and configs, and check that you can still access the browse page from caddy.
Then add your Jellyfin container and adjust the Caddyfile to proxy to it.



A so-called “neutral accent” is still an accent.