Adding this so hopefully it shows up in Google Search for some other poor soul.
I had installed plexmediaserver on Ubuntu 20.04 running in a VM on esxi, and after installation, I pointed my browser to http://plex.lan:32400/ rater than http://localhost:32400/ or http://127.0.0.1:32400/. The hostname is important here.
The symptom of my problem is that I couldn’t add media files to the server, and there was no indication of what was wrong. All I could see a button to install plex media server, and I was going insane thinking, “I’m literally connected to you!”
Browsing through logs, I got an indication that incoming request for plex.lan were being treated as being outside of the lan. I connected two-and-two together, and changed my /etc/hostname file from ‘plex’ to ‘plex.lan’, restarted everything, and it worked.
Burned through a few hours on this. May this post prevent someone from the same.