Jellyfin, AirVPN, Cloudflare and Much Ado about SSL
reddit / selfhosted

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scremmybirb · 2023-12-18 22:23

Due to my other server needs I have opted to use AirVPN with a network
lock, assigned port forwarding and DDNS. I registered a domain with
CloudFlare in order to get to the server when we are not at home. I
can get to Jellyfin beautifully, from anywhere, BUT only on http. I
have Jellyfin pointed at the assigned forwarded port from AirVPN and
then Cloudflare pointing the DDNS server for the dedicated Jellyfin
port.

I even managed to generate the key and cert to run the SSL and merge
them to the file type Jellyfin is requesting, pk12. Though SSL still
won't play and get an ssl config error at most.

My understanding is that for SSL and Jellyfin to work well together
typically there needs to be a reverse  proxy, which is doubly
complicated by the network lock and reliance on AirVPN for DDNS. Later
in the week I can afford to test with the VPN down but I want to know
it is likely going to work, and the exact maze of docs I need to be
in. Honestly confirmation that my ddns situation and a reverse proxy
have a shot is enough to keep me going.

Thanks in advance. I'm good hunting down any solution, preferably when
there is a hint it will be fruitful.