Tried copying an mp3, an mp4 as well as the iPod version of Apple's iPhone video. All resulted in this message: ""{Such and such" was not copied to the iPod... because it cannot be played on this iPod."" As a brief test, I copied a track downloaded from the iTunes store onto the iPod -- no problem. So why all of a sudden did it turn all tricky? And I had just transfered a number of CDs to it without a problem. The Mac is a G5, OS X 10.9, iTunes 7.1. The iPod is current to my knowledge ("first" 5G 30G iPod). Since the problem, I did a soft reset; haven't tried transfering again since so if that's the solution, don't know. But if that isn't, why the problem, what's the solution? Thanks, Mitchell