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ITUNES: Can't sync my purchased songs from iTunes to my iPhone

jensjakobsen asked
I have an iPhone 4S, a Lenovo T410 with the latest iTunes installed (Win 7), and authorized as well.

I can transfer most songs.

For some reason I can't transfer some songs from my iTunes library to my iPhone.

Not all songs have been purchased from my PC, and not all songs have been purchased from my iPhone.

One of those songs I can't transfer is actually bought from my wife's Mac Book Pro - but through my account and credit card.

A while back I backed up the songs my wife bought through her Mac Book Pro to my Lenovo T410 - and since all songs have been purchased through my account I presumed that I can transfer those songs to my iPhone as well?

My wife and I have the same accounts on our iPhones as well, since we think it makes a lot of things easier and cheaper.

Is this noraml behaviour?
Watch Question


You must use the same iTunes account on your iPhone as the one the tracks were purchased from.

Try managing content manually
This allows you to transfer individual tracks instead of syncing your entire library:  http://support.apple.com/kb/HT1535

Also it could be that the song is in a format not supported by the iPhone.
Right-click the song and select “Get Info” take a look what file type it is and make sure it is a supported format

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.

 (if you are afraid of restoring your whole iPhone)
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


The iPhone can only be logged into one iTunes account at any particular moment.  It looks like over the course of history you've had more than one iTunes account, and some of the songs are associated with one account, some with the other.  A lot of people got hit by this when iTunes introduced iCloud, and forced everyone away from iTunes accounts that weren't in the form of an email address.

So, on the iPhone, you may need to log out of the iTunes account you're currently logged into, and then log into the other one, temporarily, to transfer the songs.


Hi all.

Thanks for your responses :)

I'll walk through some answers to all of your questions and hopefully I'll make things a bit more clear.

- I manually manage ALL my songs -  always have.
- The song that I can't move was bought with the same account like the rest.
- The format of the song is an .M4A type.
- My iPhone has JUST been reset - this is the first time music was transferred.
- In Denmark there is no iTunes Match - no iCloud sync.
- While it is true that I have renamed my iTunes username once, the song that I can't transfer was bought with my current username.

I also cannot delete songs on my iPhone from iTunes and I cannot add more columns when I view my music on the iPhone. This is no problem when viewing music on my laptop.

Open the song in itunes & re-enter your password,etc.
Hopefully that will fix it.


That's the oddest thing: No password is required to play the song.
Oh well - I give up - no experts :(


No experts :(

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