Have to stop then start program after reboot

[bc320]

When i start up the PC it has jellyfin running in the task bar. If I select open I am met with an error saying the page couldn't load. If I stop then start the program I can access it. 

My firewall is allowing the program. 
MyVPN is allowing the program

[TheDreadPirate]

Just type into the browser http://localhost:8096.

From another PC or device you would type in http://<jellyfin IP>:8096. Obviously replace "jellyfin IP" with the actual IP of the host that is running Jellyfin.

[bc320]

To be clear, because I want to make sure I'm understanding correctly, even if I can't open it from the tray icon it is still running in the background correct?

I'm trying to figure out a permanent tunnel because of my ISP so it's not like I can easily test this

[TheDreadPirate]

It should be running in the background, yes. If you open the task manager, you should see jellyfin.exe in the process list. However, depending how your VPN is configured, you may need to setup split tunneling. It may be forcing everything, even local traffic, to go through the VPN which would be problematic for devices on your LAN or possibly even a browser on the server itself.

Are you struggling to setup remote access? Does your ISP use CGNAT?