I can draw a selection square, and then right click for context menu, but AI doesn't manage to select anything.
I can draw a selection square, and then right click for context menu, but AI doesn't manage to select anything before the menu appears.

Please accept my sincere apology for the inconvenience. Please get in touch with us at any of the other support channels – https://helpx.adobe.com/support.html . Since this is not a generic issue that we can reproduce at our end, we will need someone to look into your machine to figure out what is going on here.
Thanks
Anish Kumar
Illustrator Team
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Christopher, does this happen still when you try to right-click a selection?
If it does — can you tell a bit more about it? Not sure I understand it fully or can replicate. For me it just works.