I need some clarification please.
I have a Plex server hosted on a Ubunu server with a VPN service, as my wish is to anonymize streaming as much as possible.
As said, PMS is on a server with VPN, so all the connections outside my network are “INDIRECT”.
Is it still encrypted? Is it somehow possible for someone to find out what I am streaming?
You currently use Plex Relay. All traffic is securely routed through a Plex hosted tunnel and the bandwidth is restricted. This is because your server cannot be reached by it’s public VPN IP on TCP port 32400. I suppose that feature is missing in your VPN provider or you forgot to setup port forwarding.
However, why do you need to hide Plex traffic from your own private server to your own clients? The connection is encrypted by default and nobody else should be able to see what you are watching.
No port forwarding, i.e. your server is not accessible from remote --> only Plex Relay. Nothing you can do about it. However, does your server still listen on it’s normal public IP, i.e. does Plex appear when you access your server on port 32400? https://server-ip:32400/ ? Then please add this URL in the Plex server settings “Custom server access URLs”.
Typically, you can whitelist ports in the VPN software on the host. If you tell us more about the VPN software you use, maybe I or someone else here in the forum can tell you how to configure it properly to still allow access to port 32400.
I’m not an expert on this. However, the internet is full of questions regarding similar setups. Please take for example a look at the following link. However, always remember that toying with the network settings can get you locked out from the server. Make sure to always have a backup plan