Remote access not working with official Plex on Android

Server Version#: 1.32.8.7639 (raspian linux on an RPI 4)
Player Version#: 10.8.0.5554 (86193d4)

So I am trying to use the official Android Plex Player to access my music library outside my home network, and it almost always tells me “server unavailable”.

Now, the server reports it is available outside my network, all ports read open, and I can access the server directly via IP from outside my network (from the same phone where the app is installed). So I’m reasonably convinced it’s not a configuration problem on my server.

Plex Player shows my server, I can pin it and select it, but I have no ability to actually see my library or stream my music if I am outside my home network. I’ve attempted to set a manual connection to my IP – doesn’t work. I’ve allowed all insecure connections in case it’s some weird security issue.

I can’t find any other settings in the mobile app that might give me a hint at what’s wrong or give me something to fiddle with.

Note that sometimes it does work – but there doesn’t seem to be any indication as to why.

Using it from within my LAN always works.

It seems to be super random. I went through all the hoops of properly signing a certificate for secure connections, and the app will still randomly start and stop working.

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