Q: As soon as I downloaded iTunes 7.2 and and tried syncing my iPod, there were at least 100 songs that would not download because iTunes said that the iPod couldn’t play them. These were the very same songs that I had purchased, but had ripped onto CDs to import them again in an MP3 format for better sound quality. The past version of iTunes recognized them with no problem but this one apparently does not. The only way I was to get them back into my iPod was to convert them all to AAC.
Why is that?
A: This issue actually appears to be the result of a bug in iTunes 7.2, which several users have reported experiencing in our iLounge Discussion Forums.
Normally, if you burn any track from iTunes, purchased or otherwise, to CD and then re-rip it into iTunes, you are given the option of replacing your existing tracks or creating new entries in your iTunes library for the newly-ripped tracks. Replacing the existing tracks is often the most efficient choice, since it preserves metadata about these tracks such as ratings and play counts. However, in the case of purchased tracks, it also means that any database metadata related to these tracks having previously been protected tracks is also going to be maintained, and associated with the newly-ripped tracks.
The most likely result in the case of iTunes 7.2 is that there is some properly or attribute, likely related to the new iTunes Plus features now available, that is still seeing a need to treat these tracks as “purchased” songs, but not being able to find the necessary authorization header to transfer them to your iPod.
Hopefully Apple will release an update to iTunes 7.2 that resolves this issue at some point in the near future, but in the meantime, the most effective workaround is to delete the entries for these tracks from your iTunes library (make sure you do not delete the tracks themselves), and then REimport them into iTunes as new tracks. This should clear out any metadata stuck in the database, treating these as brand new tracks. The MP3 files themselves do not contain any information in the header other than just the basic ID3 tags such as name, artist, album, genre, etc.