I've been working on this problem for a few days now, trying to get my plex server working correctly. I have setup a reverse proxy using nginx for plex, as well as a SSL setup for my domain as a whole including plex. Whenever I try to connect to my server using https://mydowmain.net/web Plex loads the page, but then says it cannot connect to my server securely so nothing works. Navigating to https://mydomain:33400 (which is the port I use) gives me a bad cert error, saying it is only for some plex.direct URL. I haven't been able to find a solution for this after a couple days of searching and trying different things so any help would be appreciated. I am using Ubuntu 16.04, Plex Version 220.127.116.1123 , and nginx 1.10.3. I can provide more info if needed, just ask.
Thanks for any help!