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October Surprise 2016

Why can’t a 64-bit OS run a 16-bit application? – Super User

To support 16-bit programs, 32-bit Windows only generates a handles that have 16 significant bits — the 16 upper bits are ignored by the OS (even though programs are not to be taking advantage of this fact). So no program can interact with more than 2 16 objects, which is actually rather low.