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During Windows copy operation, folder already exists on destinatio?

OK, bear with me because I'm not sure how best to explain my issue.

Has anybody ever had a situation where you're copying a folder from one location to another and then in the middle of the transfer receive a "such-and-such folder already exists on the destination-- do you want to overwrite or merge" type of error?

I seem to be running into this situation a lot lately as I relocate data as part of my server (SBS 2011 standard) housekeeping and cleanup. Thing is, I am attempting clean copies of a folder from location A to a pristine location B (usually within the same volume), so I can't imagine how or why there can be a duplicate folder situation going on at the copy desination.

I've tried Googling this and haven't found anything relevant, but I know I've encountered this situation repeatedly over the past several weeks-- mainly with very large folders (multiple GB in size, lots of subfolders). 

Thus far I've just been aborting the copy when this happens pending further research, but I need to figure out how/why this is happening.

Anyone have any ideas? Many thanks.   


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