Can't sync anything from outside my network

Plex Media Server Remote Access
1

Server Version: 1.18.1.1973-0f4abfbcc

Hey there, I can’t sync anything from outside my network. It works fine internally and through VPN.
Believe it’s a firewall issue but I don’t know where to start.
My configuration looks like this:
pfSense (Ports 80 & 443 open) -> Reverse Proxy (Caddy) pointing all traffic for plex.domain.com to the windows server running plex on port 32400.
I can access the webinterface just fine, I can stream whatever I want without any troubles, I just can’t sync anything. Could it be because of the reverse proxy or a firewall misconfiguration?

2

I’ve never used pfSense or a reverse proxy so can’t say but take a look at server logs for the app request for the sync transfer. ( in console you should be able filter on get /sync to narrow it down to those lines) Should be at least a start in figuring it out.