Music doesn't sync with iPhone 4 running iOS 5. What's wrong?!!?!

[biting-mammal]

So my partner updated his iPhone 4 to iOS 5 the other day. He is running iTunes 10.5, Lion 10.7.2 and stores all his music on an external hard-drive that he connects to his computer whenever he uses iTunes.

For some strange reason, when he updated to iOS 5, no music whatsoever synced over to the phone. All that appears on the iPhone are greyed out song titles that you can't select. The iPhone says that it's got the songs there and that they're using up the capacity of the phone, but he can't play them because they're greyed out on the iPhone when he tries to select them.

We've tried restoring the iPhone from backup (3 times), unsyncing music and then resyncing it, etc. but nothing works. I thought maybe it had something to do with the fact that his music is on an external hard-drive, but his music always used to sync before and iTunes still plays the music from the drive.

Can anyone help? What should we do to fix it? It's kind of annoying that to listen to music he now has to carry around an iPod when he always used to use his iPhone for music.

 

[Trauma1]

Is "Manually Manage Music" checked off in iTunes?

 

[biting-mammal]

Thanks for your reply.

Yes, we've tried unchecking and checking 'Manually manage music and videos' and this doesn't fix it.

When iTunes begins syncing the music it freezes and doesn't go any further. It successfully backs up the iPhone and syncs everything else, but freezes up when syncing music. The iPhone says it has songs on it though, but they are all greyed out when you try and play them on the iPhone. Reinstalling iTunes didn't help either.

Are there any other suggestions?

 

[ebalazs9]

Hey.
I got kinda similar problem. I mean, my music is synchronized to my iPhone (4) but the problem is the order of the songs. So, basically all of my playlist in my iTunes is set according to the "Date Added" cat. Since I upgraded to iOS 5 the problem is that on my iPhone all of the songs in the playlist are completely the opposite what is supposed to be. So, the oldest songs are on the top, the newest in the bottom. I tried to do everything I could, "manually manage songs and video" but if i do this, the ringtones disappear from the phone. besides that it takes the mark off from videos / music / ringtones on the phone. Then I tried to roll down the iphone's playlists on the left side with the little mark. RIght now it says that the songs are in the order i requested. But they are not. I tried really, seriously everything, but does not want to succeed. I have never had this problem before, I could set it easily. I have a 1st generation ipod touch besides this phone, and it works 100% well with this settings. Please help me out, this is so annoying....
I made a picture for you (attached) to you to see that it really shows that it is supposed to be good, but IT IS NOT. :/
Thanks