I have a plex server at my house. I went to my uncles house this weekend. His login refuses to connect to my machine. I can see it trying to connect but it always fails. If I login from his machine with my account it connects just fine. So the connection works just fine. In his settings I can see that my server is shared with him and I have 2 folder shared with him. I have a plex pass he does not. My server shows up under his account but then it always says unreachable. Any clue here what is wrong? Other users are also able to connect remotely to my machine.
Your server appears to not have remote access actually enabled.
If you use some kind of VPN to access it remotely, your shared users need access to that VPN as well.
I do not use remote access like that. Plex handles the authentication to get to my server that is it. I use Swag (reverse proxy server) to handle the security certificates and forwarding of data.
I can connect remotely to my machine just fine with no VPN.
My sister can also connect remotely just fine. I am wondering if comcast is filtering his DNS somehow. I also have them (uncle) on cleanweb dns (could potentially be that I suppose)