Hi Susan,
When an order is completed, Day End will copy it to History. But because the order still exists in Current, it could still be modified.
If at this point Day End is run, it would want to copy the Completed order to history, but the original unedited order is already there. This is why the question is being asked. Typically you have edited the completed order for some reason and would want this to go to history, so you would choose Yes to overwrite. Only if you know that any edits to the completed order shouldn't be remembered would you choose not to overwrite.
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Regards,
Softrak Tech Support