I don't know if it is iTunes fault or Last.FM's fault but I think it is the latter of the two as it is a propietary software of iTunes and when it updates Last.FM should have an update soon enough. At the moment the biggest problem is that there is no actual iTunes plug-in. Instead you either use the old software that runs in the background, or you use the newest software that is an application that must be open all the time (Eff that!). Where is the iTunes plug-in? Wouldn't that make life a lot easier? And good iPod support wouldn't hurt either.