Thanks in advance for reading this post. I recently upgraded from iTunes 7 to 9 and my iPod Touch from v1.0 to 3.0 (jailbreaking the device). Everything seemed fine until I realized that 2/3 of my purchased songs from iTunes no longer play on the iTouch. When using songs > shuffle, the song and album cover appear and remain in pause mode. Clicking the play button does not work. There seems to be no rhyme or reason to the songs that work (and don't). Several were purchased for .99 cents years ago and a number were recently purchased for $1.29. The songs appear on the device when viewing the iTouch files from iTunes. I have tried deleting and adding them to the iTunes library but that does not work. All of the songs appear and play on my desktop version of iTunes. The issue has rendered the iTouch practically unusable. Has anyone run into this issue and had success resolving it?