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Issue is occurring with a RPi Pico running the most up to date circuit python, and hid library. The issue does not occur on mac machines (haven't tested linux) A power cycle of the RPi resolves the issue, however, unplugging and replugging my macro pad every time my pc goes to sleep is getting a little annoying.
I'm not really sure why this happens. I imagine it has to do with how windows handles "sleep" mode, probably still powering the device in some way, and somehow this messes with the device recognition, whereas mac probably just powers off the usb device? I'm not entirely sure..
In order to replicate this it's pretty simple:
It could very well be sending the key presses, but windows isn't recognizing them. I have no idea, and I haven't been able to see anything about it online.