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I purchased a new iPhone a couple days ago. During the setup process, I restored from a backup of my old iPhone, from about two weeks ago (the old iPhone was stolen, so the backup was a bit old). When I restored, I got a warning that 21 items could not be synced, and to check iTunes for more details. iTunes did not give me any warnings or information at all.

I noticed that the 21 songs are all songs I had previously purchased from the iTunes Music Store. They are not on the iPhone; in the iPhone music list view (in iTunes), they all have a sync icon next to them:

iPhone music list view

I can't seem to get them transferred to my iPhone. I tried removing all the music from the iPhone and resyncing, but they still were not transferred. I then reauthorized all my computers, and re-authorized my computer, but the songs would still not sync.

What's wrong? Is there a way to sync these previous purchases to my iPhone? I should note that this is not happening with all of my songs; some purchased songs were transferred successfully.

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Do the problematic songs still play successfully on your computer? –  Nathan Greenstein Nov 7 '11 at 0:20
    
Yeah, I can still play them on my computer. –  mipadi Nov 7 '11 at 0:23
    
are you using the same iTunes account on your iPhone as the one the tracks were purchased from? –  Graeme Hutchison Nov 7 '11 at 7:37
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13 Answers 13

up vote 3 down vote accepted

After trying a series of troubleshooting moves, including restoring my iPhone from an iCloud backup, the only thing that worked was restoring my iPhone from an iTunes backup, as described in this article.

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Yes, this is exactly it. Erase the all the songs from your iPhone. Do a backup in iTunes of your phone. Then reset your phone to factory settings (reformat it). Then restore from itunes backup. Then re-sync music. It should all sync. (However, some of my voice memos were duplicates and the dupes still failed to sync so I just deleted those). –  Bill Paetzke Feb 25 '12 at 3:25
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I was having a similar problem and had to go into my iphone's settings, under music, and switch on "Show All Music". The songs showed up in my playlists and then I just had to click the cloud to download them.

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That totally works!!! Go into iTunes on your phone then into purchased and hit 'not on this iPhone' at the top of screen. Then start downloading all of your missing songs!

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First of all: at my opinion this only happens with songs that you have MANUALLY deleted from the iphone ('swipe and delete' in the music app). These songs are never synched again.

Another solution (if you are afraid of restoring your whole iPhone) is this:
1. Connect your iPhone it appears in the left column
2. Select 'manually manage music' on the first tab
3. Click on the small arrow on the left side of the iPhone-icon
4. Go to music
5. Delete all 'greyed out songs'
6. Go to your music library, select the songs you want so sync and use Ctrl+C to copy
7. Go to your iPhone -> Music again and paste the songs (Ctr+V)
8. The file is copied to the iPhone
9. Turn 'manually manage music' back off, if desired

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Rename the title of the tracks that are not transferring. You can add a "1" at the end of the title or even add an extra space at the end of the title. For example: "Baby one more time" to "Baby one more time " or Baby one more time1". Once you rename it, try syncing. This worked for me!

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I had the same problem, and I solved it by adding all the songs that were grayed out to a playlist. Have your iTunes set so that you manage your music manually and delete the gray songs off your iPhone/iPod. Add the gray songs to a playlist and drag the playlist into your device. This adds all the songs you wanted to your music player, and once that's done syncing, you can disconnect it from the computer and delete the playlist. Voila, your problem is solved.

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I had the same problem but I just know how to solve it. You simply uncheck all the songs in iTunes and sync. Then all songs in your iPhone are gone, now check all the songs in iTunes again then sync. Everything will show up in your iPhone.

When you hold the command key down, clicking one song's check will toggle all the selected songs (the entire library if you haven't narrowed the search).

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are you using the same iTunes account on your iPhone as the one the tracks were purchased from?

You could also try locating the original files, convert them into another audio file type, and then put them back into iTunes.

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Yeah, same Apple ID and everything. –  mipadi Nov 7 '11 at 15:39
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The best fix may be to download fresh copies of the previously purchased music. Log in to iTunes Store and click on "Purchased" on the right side of the iTunes store.

On this page, choose Music and your purchased songs will appear. Ideally, you can choose "Not in my Library" which should display the 21 missing songs.

Then download all. With freshly download purchases from Itunes Store, they should now sync. Here's Apple's link on the topic.

http://support.apple.com/kb/ht2519

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In iTunes, nothing appears in the "Not in My Library" tab (which makes sense, since they are in my library). When I re-download them using the iTunes Store app on the iPhone, I just end up with duplicate entries -- the songs no longer sync. –  mipadi Nov 7 '11 at 15:41
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I guess I could delete them from iTunes and re-download, but then the play counts and other metadata will be reset… –  mipadi Nov 7 '11 at 15:41
    
I just re-downloaded a song I purchased which appeared under "All" and was already in my Library and it worked. I now have a fresh version in my Library. Try it with one or two of yours and see if that resolves the puzzle. –  bg2011 Nov 7 '11 at 22:49
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I tried redownloading it on my iPhone, but it didn't sync up with the copies in my library. I can't force a redownload in iTunes; I can delete the songs from my library redownload them, but I'm hoping to find another solution, since I don't want my play counts and other info to be reset… –  mipadi Nov 11 '11 at 2:41
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I had the same problem. Turned out I had just used all of the phone's storage. Deleted a few photos and they started syncing.

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Valid point, but the OP states that he deleted content on the iPhone before syncing. –  patrix Oct 15 '12 at 15:28
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It may seem strange, but I solved this problem by going to iPod → Music → then checked Include music videos and Include voice memos. Doesn't make sense but it worked.

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I see that this thread is several months old so I'm hoping this will help those that experience this problem in the future. I was transferring music from my iTunes to my new iPhone and I noticed several songs weren't able to be transferred to my phone even though they were listed as such on iTunes. Similar to the user above, the songs that wouldn't transfer were "grayed out" with a "sync" icon listed next to each untransferrable song.

This is what worked for me: In iTunes, I simply clicked on my iPhone (for anyone else it will read "YourName's iPhone") and then clicked the "Sync" button on the lower right-hand corner of your screen. Doing this immediately synced the untransferrable songs on my iTunes to my iPhone.

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I had the same problem described here, but syncing and other suggested solutions just weren't working.

My solution (discovered by accident) was to open up iTunes ON my iPhone. Once opened I clicked on "Purchased Music". You'll see that although your iTunes on your computer has downloaded it, you phone hasn't.

On my iPhone I then started clicking on the box next to each song in "Purchased albums" that hadn't downladed. The phone immediately started the process of transferring them onto the phone.

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protected by gentmatt Sep 22 '12 at 18:09

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