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Port 8096 is the default HTTP protocol port, and you're trying to access it via HTTPS. Do you have certificates installed and available for your jellyfin instance? If not, it's very likely Cloudflare won't route it correctly.
I'm not saying this is your specific issue, but it'll be the one after you fix this one at least. You may need to mess with the cloudflare "current encryption mode" to get this to work.
I'll try swapping it to http unless you think I should run nginx or something to certify it. I don't know if that will help.
I always advocate for HTTPS. I run a caddy proxy and sidestep cloudflare all-together.
I assume a Caddy set up would get me a URL? I might look into that.
Correct. Mine is 'jelly.domain.com' which bidirectionally forwards traffic between my domain and my home server.
You don't need caddy if you're running cloudflare tunnels.
Fair, but if I'm technically violating TOS and CF tunnels aren't working anyways, I might as well try it.
I run caddy to handle https certs. Works great and it's incredibly easy to setup