Calculator is not a good beginner app for several reasons. I would use Notepad if you just want to write your first automation. The reason it stops is because Calc.exe no longer exists in Windows 10. If you run that, it actually launches Calculator.exe. In order to hook that , you'd need to set the path to wherever Calculator.exe is. I also think there's some further complication there as it is a virtual app and gets installed with Windows updates, although I haven't tried in years.