All my music is in iTunes. Some was purchaed on iTunes, some on Amazon and some loaded from CD's. Synching was never a problem until recently. New purchases did not seem to synch even though checked in the box. I unchecked everything and synched which wiped the phone clean. Then tried to synch the entire library. The song, artist information fully transfered but all songs show in light grey and are not actually loaded. About 5% of them did load, listed in bold black type and play. When in iTunes synch mode, looking at songs in the phone, the computer also shows them in light grey with a small circle in the left collumn with a little i in the middle. Mystery is that all these song have loaded to the phone in the past and the 5% that does load is not just iTunes purchaed but very random. Example: only one song from a CD loads and the rest in light grey and not actually loaded.