iPhone 4 (iOA 4.3.3) , MacBook Pro (10.5.8), iTunes 10.3. This stopped working after a security update. I use play lists that adjust my music according to date and play count. It keeps the play list fresh for me. Yesterday I noticed the music did not sync. I rebooted the phone; no luck. I rebooted the mac and it worked then and again this morning. This evening it did not work. I reinstalled iTunes, rebooted the MacBook Pro, rebooted the iPhone. No luck. The security update was applied 28 June. This may be the cause of this problem. Has anyone else noticed this behavior.