Form past memory, it might be an issue with another app holding the clipboard, IIRC on Windows the clipboard can be held and then requests to update it can fail. IIRC there was a discussion on that in Scintilla, I'll have to check what's the difference between the menu and the shorcut (likely none) but if it's that timing issue you can either just be lucky with the menu, or opening a menu does something on the Windows side.
If it's a locking issue, it's unsure we can do anything about it, or if we should -- if another app was holding it, why would we override it? Well, one cuold argue that if it's already locked we're trying to change it last and should win, but then why having a locking API anyway? Meh.

Either way, please check if you don't have another software running that is the cause of this (clipboard manager, or any other app that would get setuff in the clipboard).

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