Some typing / key pressing issues with and without modifiers

I've confirmed that this method does work with holding ⌘ and pressing Tab to activate the macOS Application Switcher. However, the version I posted in this link simulates holding ⌥ and pressing Tab, so should (in theory) work in Parallels, assuming System Events conditions are indeed passed to the VM.

Great. Thanks noisneil ! That works now ! As Feedback for others: The macro for the "forwarded" Tab Key also needs to contain the option modifier being selected...

The AppleScript Delay is pretty noticeable though as you already mentioned...still can't understand why KM is not capable of performing such a stupidly simple task with the "Press and Hold Modifier" action and why this action is implemented in such a strange way...

It's already been explained why, since the removal of kexts by Apple, almost nobody can do this "stupidly simple task" any more. Software event =/= hardware event.

So you'll have to work around Apple's imposed limitations by using System Events from an AppleScript. Exactly why this works can -- perhaps should! -- remain a mystery. I'd only note that Apple have a long history of breaking their own rules...

Happy to hear that it works. Unfortunately I think it's a case of living with the AppleScript lag or looking into alternative solutions.

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