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you are juggling 2 OS + different builds + different versions of calibre
is the win 8.1 PC a separate PC from the win 10 one ?
if so I'd try to debug the calibre issue on that w8.1 first.
most likely you have some other software on both PCs that is interfering with drag and drop , or you are drag+dropping across different drive types ?
If you post your exact w8.1 config i.e. 32 or 64,& calibre version and also whether that is 32 or 64, + your HD config,+ your calibre library location, there will most likely be someone here with an identical set up , so you can compare results with.
you are much less likely to find anyone on the same w10 insider build numbers
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