@majortriad I was going to introduce this as a troubleshooting step later, but since ChuckPa mentioned it… You can see what connection information has been published for your server to Plex by navigating here in your browser (if using Safari you must enable developer tools):
https://plex.tv/api/resources?includeIPv6=1&includeHttps=1&X-Plex-Token=your-plex-token
Replace “your-plex-token” with your Plex online token, which you can find by following the instructions in this article:
https://support.plex.tv/articles/204059436-finding-an-authentication-token-x-plex-token/
The resources page will show all of your signed-in devices along with their connection information. For your server, you should see an entry that has your TrueNAS host machine’s private IP address. It will likely also have one container IP address as well.
When a client device is opened when signed-in, it retrieves the list of connections available to it. For servers, it then attempts to connect to them trying local options first, in my experience at least. Failing that, clients then attempt non-local connections.
