"Execute a Keystroke" for the SHIFT Key?

Questions & Suggestions
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I do not think that is possible because the Karabiner Elements EventViewer does not recognize StreamDeck buttons.

You might consider having the Streamdeck button set off a KM macro, then have the KM macro detect whether a modifier button on the keyboard is pressed - based on that the KM Macro can proceed accordingly.

Or you could use a keyboard or mouse with programmable macro buttons instead of the StreamDeck.

Or you could use the Logitech Farm Sim device Logitech Heavy Equipment Side Panel -- The ultimate customized USB input device? instead of the StreamDeck.

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