In the VMware window, when I open, say, the Windows app Notepad, I can clearly use the physical keyboard to type. But when I instruct Keyboard Maestro to type (either by Type a Keystroke or by Insert Text by typing) the keys do not reach the app inside VMware.
Somehow VMware can distinguish between typing on the physical keyboard and Keyboard Maestro "typing" virtually. How can VMware do this and how can I get around it?
I probably won't have the best answer, but I definitely have a thought. Try opening the MacOS Keyboard Viewer and see what happens when you click on keys in that special app. If you don't already have the Keyboard Viewer Icon in your Menu Bar, you have to set that up in System Preferences. However since I don't know what version of MacOS you are using, I can't tell you which pane to open in that app. For me it's under Keyboard / Input Sources / Show Input Menu.
If the Keyboard Viewer works in your client (ie, you can type into your client using this app), I may have a workaround idea for you. You probably won't like my workaround, but every little step forward might bring us to a solution that will work for you.
I'm not sure what it means yet. I just thought it would be a good test. It has provided some important data that could lead us to understand the problem and/or solution. I'm still contemplating. it. I'm not sure if I'll have an answer, but your theory is also my theory. I just thought this test might help prove or disprove this theory.
A second theory is timing. Many apps have timing dependencies that require finessing in order to get input to work correctly. If you try inserting Pause statements around some of your input attempts, you might get better results. But in this case I don't think it's timing.
Actually, partially it is timing: When I insert 0.5 sec pause at the beginning, just before the key stroke it works somewhat. I guess VMware then has time to give focus back to the remote app after it lost focus from the Keyboard Maestrotrigger??? However, shifted key strokes don't come through properly.
So I'm giving up on it with Keyboard Maestro. - Maybe I'll experiment with Karabiner-Elements instead. It is a bit more low-level...