I've owned a few ipod's also and I would agree, they seem to cope with gapless playback no bother. I haven't actually tried this on the Sony as I've actually stopped using it after only 2 weeks because of an even bigger issue I just cannot abide. The sound normalization which is supposed to correct the difference in volume levels, just does not work properly. On louder songs, it will reduce the volume during the song if it starts off with a quieter instrument such as acoustic guitar. When the remaining instruments come in later, the Sony cuts the volume as it suddenly realizes it had the original part of the sound too loud. This is soooo annoying and considering the ipod, itunes and Windows Media Player can do this simple task without any problem, why can't a giant company like Sony not sort this out. I have wasted £300 on this Walkman as I cannot use it. Surely the whole idea of digital music players is that they can store massive amounts of music, play them back in whatever order you choose and using clever software should be able to keep them the same volume! I have now purchased a new ipod touch and my Walkman is heading for ebay!