I tried using a WAN connection and it works. In fact, since my plex server is on different VLAN, I just opened port 32400 from my device. I have split DNS configured so that if from outside I can hit it via port 443 and traverse it to 32400/TCP via proxy. For my internal network, I am taking out any proxy and have it automatically go to standard 32400 port. What I don’t understand is why the implementation is different between IOS and Android. Android works flawlessly with the current setup.