Cannot Connect to Plex with Secure Connection

well this might be a bit out a stretch but is your data center on a static or dynamic ip.

are you accessing your plex Via app.plex.tv or localhost:32400
have you ruled out any double Nat is your server on a static IP. port forwarding is also needed in the router and all hops to your server from a publicly accessibly IP.

might want to read thur Secure connection? and similar next