A system, apparatus and method of appending a group of files to files on a clipboard of a desktop are provided. The system, apparatus and method include displaying a first window having an option that allows a group of files to be appended to files on the clipboard and asserting the option to append the files. The first window is ordinarily displayed after at least one file has been copied onto the clipboard and a second file is selected to be copied. In the case where at least one file has not already been copied onto the clipboard, a second window is displayed. The second window has an option that allows only one file or group of files to be copied onto the clipboard. The first window further contains an option that allows a file or a group of files to replace file or files already copied on the clipboard.