I seem to have made some progress in my troubleshooting, but haven’t found the final fix yet. Following the advice in Not Authorized / Unable to claim server - FreeNAS I was able to get the Plex server to a point where it actually tells me ‘This server is unclaimed and not secure’ and shows me the ‘Claim Server’ button. However, clicking ‘Claim Server’ doesn’t do anything. Going into the server log file, I see requests going out to plex.tv using an old IP address: ‘Request: [192.168.1.245:58262 (Subnet)] POST …’ 192.168.1.245 used to be my server’s DHCP provided IP address a long time ago, until I changed it to fixed address 192.168.1.21. Now I need to figure out, where the server on my NAS pulls this old address from and how to fix it. Anyone have a pointer? I hope that is the actual problem.
