I think I mention half-way down this post in green text here How to transfer music to my iPod (& iTunes) {click on link} how to set it to automatically transfer to iTunes & auto add to its library. However beware, iTunes only imports mp3, mp4/m4a, aiff & wav files. iTunes will not import wma, real files, ogg vorbis, mp3pro, any of the lossless compressed formats such as flac or monkey (ape), etc. & will also not import virus files pretending to be viruses afaik.