If you go to any folder, right-click an executable, and select Pin To Start, it won't happen.
If you do it from within an Explorer window, it does.
Pin To Start not working from TC.
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Re: Pin To Start not working from TC.
It's a known Windows bug, it also affects other programs and only works in the Explorer. See:
https://www.ghisler.ch/board/viewtopic.php?p=299218#p299218
https://www.ghisler.ch/board/viewtopic.php?p=299218#p299218
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