Is the only way to connect remotely via Roku is Reverse Proxy?

[fontmasterflex]

I'm working on setting up a media server for myself that I would eventually like to give access to, to my parents who live 250 miles away and use a Roku for streaming. They are not especially tech savvy. So for now I'm doing a trial run of Jellyfin just on my desktop computer. I've got everything worked out for local network. works fine (minus my bonus question later) so far, I am grasping what is going on. 

I am, however, having a difficult time understanding exactly how to make this work remotely. From what I can tell, there are only two ways to make this work via Roku on their end. Reverse Proxy via something like Caddy, that I would install on my machine? Or just opening ports, which i understand is bad for security. 

Are these the only ways I can do this with the end user being on a Roku? Pretend I'm a total noob idiot. In fact, don't pretend. 

Second question, I have a tv show that i have .mkv files for that I can't get to show up in my libraries. i've tried resetting jellyfin, double checked the path is correct. I was under the impression that Jellyfin could play .mkv files?

*Edited to add: I've looked through all the tutorials I can find, but don't see any that pertain to Roku and remote. Sorry if there's already a post covering this.

[TheDreadPirate]

Caddy is the easiest and safer way share your jellyfin server. You'd need to get a domain from whatever provider you want. DuckDNS provides free addresses, in addition to having a client that ensures your domain is updated if your public IP changes.

Caddy also automates getting certificates to allow use of https for remote connections. Which requires port forwarding port 443.

Then you create a jellyfin account for your parents and have them use your DuckDNS address to connect.

Jellyfin does support MKVs. If you can't add it to Jellyfin, double check that Jellyfin has permissions to read it.

[fontmasterflex]

Caddy is the easiest and safer way share your jellyfin server.  You'd need to get a domain from whatever provider you want.  DuckDNS provides free addresses, in addition to having a client that ensures your domain is updated if your public IP changes.

Caddy also automates getting certificates to allow use of https for remote connections.  Which requires port forwarding port 443.

Then you create a jellyfin account for your parents and have them use your DuckDNS address to connect.

Jellyfin does support MKVs.  If you can't add it to Jellyfin, double check that Jellyfin has permissions to read it.

Thanks for your help! The MKVs ended up working on their own... idk what the deal was there. 

I did also get everything to work getting my mom connected remotely through the Roku. I'm currently waiting to hear from her if she can STILL access though because I've tried accessing from a computer at work to try and show off a little (DOH!) and I can't get the jellyfin player to connect to my server. Just gives me the "can't connect, make sure it's on", which I have. 

Any ideas? I'm not at home so can't tinker from here, but just seeing if I maybe am overlooking something. 

Thanks for the help broseph!

*EDIT, My mom can not find the server now. I know the computer is on. wondering if the portforwarding closed somehow? strange...

[TheDreadPirate]

Check that port forwarding is correctly set for port 443. Make sure that they are using "https://yourDDSAddress". Make sure that port 443 is open on the host firewall.

Also, never show off until you verify it is working.

[fontmasterflex]

should the https port be the same for local and remote? my local port for https is 8920, but public is 443.

So I ran Caddy again and it opened those ports back up (checking on portchecker.co) and mom was able to get in. there were errors in retrieving the data though, but i suspect that's simply an internet speed issue?

I have a feeling the ports being open is timed. i didn't change anything from the first time i successfully was able to have my mom connect and when i commented this morning. I'm admittedly way over my head in this stuff, but it's fun learning. i sure appreciate any input you have. thank you