Amber, thanks for your response but I'm not sure I understand. I'm not sure of the relevance the new version of Apple's iOS5+ since we are transferring from a Windows computer. The duplication occurs on the Windows computer. Before the transfer is initiated, there is only one file, lets say "IMG_5671" that we wish to copy to the iPad. After running your transfer application to copy it from the My Pictures folder on our Windows computer, a file "Copy of IMG_5671" is added to the My Pictures folder on the computer (the picture is transferred to the iPad successfully). So my questions were and are, why is this creation of a copy of the transferred file on the Windows computer happening and how do I prevent it?