iTunes fails to transfer all tracks to the iPod

Q: I’ve had a sad run of bad luck with my computer hard drives resulting and several reformats, a new computer, another reformat and then yet another new hard disc! Now I find that iTunes will only copy a few of my songs to my iPod even though there is plenty of spare capacity. I suspect that there is some sort of copyright rule coming into play. Can I fix this without reloading hundreds of CDs?

– Warrick

iTunes fails to transfer all tracks to the iPod

A: This likely isn’t the result of a “copyright rule” per se, although if you have purchased tracks from the iTunes Store it is possible that you haven’t “authorized” your new computer to play those tracks. This is the most common cause of tracks failing to transfer to the iPod after reinstalling iTunes onto a new computer system.

Note that iTunes will normally provide a warning message when tracks cannot be copied to the iPod for this reason or any other reason.

If you are not seeing any warning messages, try right-clicking on your iPod in iTunes and choosing the “Reset Warnings” menu item.

Once this has been done, simply sync your iPod again. If there are any problems preventing tracks from being transferred, iTunes should notify you of this.

If the issue is with transferring purchased tracks, this likely indicates that you will need to authorize your computer. iTunes will not transfer any purchased tracks to a connected iPod unless the computer that you are using has been authorized to play these tracks.

This normally occurs the first time you attempt to play a purchased track. If you have moved to a new computer, however, your authorization keys will not necessarily be restored as part of your iTunes library.

To re-authorize your computer, either try playing one of the purchased tracks, or go to the Store menu in iTunes 7 and select Authorize Computer. In either case, you will be prompted to enter your Apple user id and password for the iTunes Store. iTunes will then download the necessary authorization keys to allow your computer to play these tracks and transfer them to your iPod.