Can't access Plex server from web app

Just rebuilt my server and I’m finishing up setting things up when I noticed I can’t access my server from app.plex.tv/desktop. It’s giving me app.plex.tv is unable to connect to "my-server" securely. I have no issues accessing it from the local instance and I even checked if I could access it from Plex HTPC and that worked too.

I’ve tried toggling the settings for insecure connections in Settings > Network > Secure connections from Preferred to Required and back again, but that didn’t do anything. I’m not connected to a VPN, although I did try that and that didn’t seem to work. Tried Firefox and Chrome and neither work. Any ideas?

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