Provided is a technology to scan a document for file attachments, generate alternative file names corresponding to a particular attachment, determine whether or not the particular file attachment is the latest version of a file or has a name and/for file path that could he confused with the name and/or path of another file. In the event one or more of the above conditions is met, techniques are also provided to verify that the file attachment is the desired file and, if necessary, to select an alternative file for attachment.