Reply To: Refusal to Replace Existing PDF

Is the error it gives “the file may be open or in use”, something like that? Are you part of a network with several computers?

When it happens again you can try pressing “Cmd,” “Opt” and “Esc” together, and see if Adobe Acrobat or the file is listed in there somewhere. You would then choose force quit on it to make sure it's really closed, then hopefully it lets you overwrite.