Run Core As Windows Service

This is not rocket science.
Just start windows Task Scheduler and create a basic task. Follow the guide, at the end (Finish) remember to check the “Open the Properties dialog for this task.” This will give you the dialog box stated above.
I have been running this for almost one year on my headless sever. My server is running server 2012R2. Starting ROON by the task scheduler can be used on Windows 10 as well. My server is booted every day by sending WOL package (wake on lan) and shut down by a remote windows command. The startup of ROON has never failed and upgrade/update of ROON has been done without any issues. My Music library is located on a Synology NAS.

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