Setup a Plex server on Debian
On your Debian server
Download Plex media server:
wget https://downloads.plex.tv/plex-media-server/1.13.5.5332-21ab172de/plexmediaserver_1.13.5.5332-21ab172de_i386.deb
Install Plex media server:
dpkg -i plexmediaserver_1.13.5.5332-21ab172de_i386.deb
On your Windows machine
To perform the initial setup the Plex GUI needs to be accessed locally, a step only needed once. To do this you can establish a SSH tunnel using Plink:
plink.exe <REMOTE_IP> -P <REMOTE-SSH-PORT> -L <LOCAL-LISTEN-PORT>:<REMOTE-FORWARD-IP>:<REMOTE-FORWARD-PORT
Assuming your Debian server has the IP address 158.6.150.13, SSH runs on port 22 and Plex is locally accessible via 127.0.0.1:32400 on your server:
plink.exe 158.6.150.13 -P 22 -L 127.0.0.1:8888:127.0.0.1:32400
You can now access the setup page by browsing to http://127.0.0.1:8888/web on your Windows machine. The browser will connect to the server as if it were local and load Plex Web App”