[Good practice around Windows Graphical App?

I’m using vagrant to run a windows app, that will peform some automated task and then will shutdown.

I have been running on issues while automating the execution of the task with trigger.ruby and trigger.run_remote for multiple issues but mostly because graphical apps are finicky in terms of console ownership and other permissions.

I am trying now with a startup app creating a link in C:\Users\vagrant\AppData\Roaming\Microsoft\Windows\"Start Menu"\Programs\Startup\ but even this is not exempt of gotchas as the app will run before the volume mounts are setup for vagrant.

Are there any good practices around how to execute graphical apps from vagrant?