Hi, I am not sure if this question has been answered but my dad has a iPhone 3g firmware 3.0 jailbroken that just recently stopped syncing with itunes. He has a playlist that he always adds new songs to and syncs that playlist. However, now when we add the songs to the playlist and press sync there are no changes that occur. Also, before I was able to play the songs when I clicked on the Music tab under his iPhone on the navigation pane on the left side of iTunes. Now all the songs are grayed out. When looking at the iTunes summary page when the phone is plugged in neither "manually manage my music" nor "sync selected folders" is checked. I tried to chnage those settings but I was still not able to sync the songs. I am pretty sure he didnt change any of the settings so I am not sure why this is. FYI, he is using a windows computer with the latest version of iTunes. I wanted to get some input or thoughts before I go through with restoring the whole phone. I wanted to avoid that. Thanks!