Same problem here, but ALL of my music is greyed out and will not play. Both the music I purchased on itunes and that which I burned from my CD's are greyed out and inactive.
Here are the things that I've tried based on suggestions on this web site:
Powered the phone off and on
Synced multiple times
Uninstalled and reinstalled the 10.5 upgrade
One suggestion that I got at work and have yet to try: authorizing and deauthorizing my PC (Windows XP 32-bit).
Apple: This is obviously a bug in your upgrade; please fix it!
One way round it I've found is to select the option to convert them all to 128kbps on sync, which means they all transfer over fine, but this is only a temporary solution, 128kbps is not great quality if I want to airplay the music to a hifi. This suggests to me that for some reason ios5 doesnt like some of the original files (even though itunes and the ipod classic does) and the sync breaks for some reason relating to that?
Ok i think i have found out how to do it. Unplug your i phone, go to settings and then reset then reset all data and settings. This will warn you that it is going to erase eveything on your phone.
DO NOT BACK UP BEFORE HAND
then restart your phone and restore back up from when you donwloaded the new IOS5. This should sort out your problem :-)
Had the same problem. Talked to Apple and they suggested a few things. In the end, what worked for me was not the restore, but unchecking all items to be synced (i.e., music, books, audiobooks, etc.). Then I slowly dragged individual songs, then playlists from My Music to the iPhone. This did the trick in the end, and now it's syncing OK
Same issue here. Struggling with trying to fix it. I set my phone to manually manage music, and was able to drag files over. Although, some of the files would not copy the first time, so I had to delete them from the list (they were still greyed out) and do it again until it worked. There definitely seems to be some sort of bug here that needs to be addressed by Apple, as I would really like to be able to use the automatic sync as intended.
I have been fighting this problem with both my iPhone, my partner's, and my nephew's. It seems to have something to do with music purchased in iTunes vs. music that is ripped, since all my ripped music transfers fine and stays put.
On the other hand, downloaded content shows up doubled (one black, one grey) when I look at my music through the iTunes, just like that screen cap. As long as there's a "black copy" showing, it plays fine on my iPhone 4s, but I find I have to remove the greyed out copies manually and then manually transfer from my iTunes library or from the purchased option on the phone itself. In other words, if the music on the phone in only greyed out copies, and it's not on the phone, it doesn't transfer manually unless I first delete the greyed out versions. -- And then the greyed out versions magically reappear after it contacts the cloud and backs up.
I also sometimes end up with doubled copies, and my albums don't all sort the way they should -- so for example some Diane Schuur shows up under the artist name, and some shows up under albums. To put it all together I had to make a playlist, which is stupid.
Finally, there are some 46 items it tries to sync everytime I do any wi fi syncing of anything with my phone. I have no idea what that is.
I'm tempted to wipe and let all iTunes content be restored from the iCloud, a process that would require an overnight restore. I'm guessing that might solve the problem, but why should it all be this hard? Does Apple look at these comments, because I notice there are several different threads on this site concerning the music app and the iTunes/syncing issue?
I too have this problem randomly with my new white iPod Touch, and it has nothing to do with purchased or ripped music - most of my failures come from freshly encoded m4as.
I also have problems with drag and dropping music into iTunes - those files might end up in the playlist, but they WILL NOT show up in the library itself, which results in those songs not syncing to my iPods. I figured out a solution which _usually_ works (File > Library > Import playlist (m3u)), but this is absolutely unacceptable when you consider that iTunes 10.4 had no such problems.
I did fix the problem, but it required a radical solution.
1. Delete all music from the iPhone
2. Do an iCloud backup.
3. Open iTunes, plug your iPhone in and do a DFU Restore (Google it -- it's a deep restore) or better: go here
4. When the phone finishes restoring, go through the menus, put in your Apple ID, and restore the phone from your last iCloud backup.
5. After the phone is all done downloading content (this can take some time), manually drag all your music over.
6. When I did this, everything was fine, but that iTunes ran a whole second sync of its own (without my prompting it) and made a mess of everything -- putting back greyed out copies, etc.
7. But -- I just spent an hour getting it how I wanted and eliminating all greyed out copies (keep in mind, music won't copy to the phone if it has a greyed out copy of it already in place).
8. As I've continued to add and sync music, the greyed out copies HAVE NOT RETURNED. I think it finally fixed the problem.
9. My theory is that the original iCloud backup had its own ideas about where the music was supposed to be, and once I made a backup without any music, it has allowed me to organize it my way.
Tomstevens_uK turns out to have about the right solution, not the convoluted mess I said above, and which didn't work. My iPhone reverted to the same greyed out stuff after a day. The "Geniuses" said the problem comes from corrupt data in the back up. I've been dragging the same data along since my 3G, and it was finally time to just start over. So, do an iCloud back up, copy as much data as you can off your phone (for example, import your camera roll -- it will be destroyed -- I also used screen caps to save time remembering my email settings), do a DFU restore (see my post above), and do NOT restore from iCloud backup, but just start it as a new phone. Since you did backup to iCloud, when you log in with your apple ID, it restores your contacts, reminders, calendar info and other vitals (like your phone number!) but otherwise it's a brand new phone. Manually rebuild all the apps and all the music. Takes a while -- but everything works perfectly now, and I swear my phone even runs better. My old phone photos now appear as an album, just like the others.