I wear a pair of Loops Experience most days in the office https://www.loopearplugs.com/products/experience

Can you set the Jellyfin server service to start with Windows? Shouldn’t need a login then. If not, you can use a PowerShell script that starts the Jellyfin .exe and use a scheduled task to run it when event id 6005 is triggered. That’s the event id created when the event log starts.