Purchased Songs from iTunes will no longer sync to iPhone 4s.. any help on this ?

. All that music is in Music library on iTunes and plays well has been purchased with the same Apple id. On Windows -7, iTunes 10.5.
. Under previous purchased icon on iTunes all music shows downloaded.
. Unchecked music Sync from iTunes > removed all songs from the phone.
. Tried syncing manually just 1 song and got the same error "1 item could not be synced check iTunes for explanation " and there is no message on iTunes.
. We deleted all the Songs from iTunes and now re-adding.
. If this does not work then I will be testing with re-creating a new Library and testing in a new user account..
Does anyone have a better idea...?

Hi firmflange,
That definitely sounds frustrating! I have actually encountered this same behavior in the past, and switching out the USB to 30-pin cable was the resolution (hardware issue with the cable). Does the same behavior occur when you use a different cable?
If so, we may need to troubleshoot the USB connection on your computer. Refer to this article:
iOS: Troubleshooting USB connection
http://support.apple.com/kb/TS1286
Thanks,
Matt M.

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    Click on the link to see more details and screenshots.
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