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HTTPS with FreeDNS (self.selfhosted)

submitted 9 months ago by ProtecyaTec to c/selfhosted

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I feel like I have a doozy of a complicated issue and am looking for some guidance.

I'm new to Selfhosting so I got myself an off-the-shelf Asustor NAS. It's got apps which is cool, so I've installed Jellyfin. I want to access my Jellyfin over the web so I've set up DDNS via my Asusstor Manual Connect and FreeDNS. This works well, I can access it over HTTP but the domain is... kind of long and unpleasant, so I got myself a "pretty" domain and setup a CNAME to the FreeDNS. I'm port forwarding on my router, everything works, so far so good.

To make it overtly complicated, I want to make the connection HTTPS. This is where I'm struggling. I've set up the SSL cert for my "pretty" domain via Lets Encrypt, but it times out. I'm not sure if, or how I can make the FreeDNS HTTPS or covered under my Lets Encrypt cert since I don't technically own the FreeDNS domain. My provider doesn't give my any wildcard options on the "pretty" domains cert either.

I've got the HTTPS set on my Asustor and Jellyfin based on the "pretty" domains SSL cert. I've got my port-forwarding 443 to Jellyfins suggested HTTPS port on my router. I feel like the lynchpin is the FreeDNS subdomain handing off the DDNS request but I'm not sure how to solve it. Any suggestions on how I can get this setup to work? Anyone else run a similar setup where they access their local X port via the web via HTTPS?

Open to similar experiences, suggestions, ideas, pretty much anything at this point.

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[–] ProtecyaTec 1 points 9 months ago* (last edited 9 months ago)

I don't know if this will help anyone but damn is the documentation on how to do this kind of thing scarce so here I am. I was quite a struggle both learning all this and implementing it but it's been fun overall.

FreeDNS doesn't seem to have a way to add any kind of SSL Certs as far as I can tell. Not that I needed to, but when I tried explaining my situation to the hosting provider they suggested that the cert needed to be on the DDNS server.

I also couldn't get the Asustor Reverse Proxy to work either. Many of the tutorials and user suggestions i ran across suggested that this is the way to get SSL but when I tried to implement it I kept landing at my portal login and nothing was getting proxy'd. The netstat command was showing that whatever the reverse proxy port needed was not open - I also ran across this in a 2020+ thread on Asustor.

Right now I'll also need to manually update the certs and go through this process again in 3 months time. There might be a way to automate this process but it's a lot of steps that I'm not sure can be automated in this seeming (to me) flawed setup. In any case, it's been challenging but fun and I think in the next 6 months I'll upgrade out of Asustor and into a bigger server with a core Linux setup. I know nothing about Linux :)