Unable to access server via plex.tv or iOS app

Plex Media Server Desktops & Laptops
1

Server Version#: 1.13.5.5291
Player Version#: 3.57.1
OS: Debian Stretch Stable XFCE

I am running into an issue where I am unable to connect to my server on a remote network with a secure connection via plextv or the iOS app. Using my WANip:32400 works just fine and connects securely. Using an insecure connection allows plextv to connect and stream just fine.

https://drive.google.com/open?id=1WNBk_Z8P1_AK2v038wXVbGBX3mDvHnpF - log files

Ive used NetworkManager to set a static IP address but even with DHCP enabled it still errors out. I am able to ping www.plex.tv with no issue from the server.
Hosts file is default

Does anybody have any advice?

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