NGINX and Jellyfin

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Oh boy...I didn't catch that to begin with. Any networking changes will generally require a restart of Jellyfin (at least). No idea on the NAS front, that would be specific to their software. Looking at the networking section of Jellyfin's admin dashboard I wonder now if the issue may have been not putting the custom address in the base URL area?

With RP, and it's different with a lot of them, but most are set up for either subdomain or subfolder (e.g., jellyfin.mydomain.com or mydomain.com/jellfyin). The base URL section is required if you use subfolder setup (the latter). If you didn't have "/jellyfin" in that area, it makes sense that it wouldn't load properly. Not saying this is 100% the fix, but if you BACKUP YOUR SETTINGS and want to try again, this might be your solution.

The custom port would have needed to be set in the Docker image (i.e., in Portainer you would set that 8096 in the container is equal to something else outside of the container). This is a common practice to avoid script kiddies looking for common services to attack, but it's not a big deal if you secure Jellyfin with strong passwords for user accounts. If you didn't set a custom port on the container, you can't use a custom port within Jellyfin or on the RP -- it'll just break. You'd also use the HTTP port since the RP is taking care of HTTPS (Jellyfin isn't accessing your SSL cert directly and handling HTTPS).

I know jack shit about all of this and have been inferring it from research, experience, and osmosis from experts. So take my explanation with a block of salt until somebody else (who knows what they're talking about) says I'm right or corrects me...