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.
Converting them to AAC will also work, as you’ve indicated, since you are again creating new library entries for these tracks. However, re-converting them to AAC will result in a reduction in quality, so it is generally a less desirable option.
The only disadvantage to either of these approaches is that you will lose any ratings, playlist, or play count information for these tracks.
As a side-note, burning and ripping iTunes-purchased tracks as MP3 files (or any other format) will actually not give you any additional quality, since the AAC lossy compression format these tracks came in has already resulted in audio information being discarded which cannot be regained. Therefore, while burning and re-ripping tracks to MP3 is a useful way to allow you to play them on other devices that do not support AAC or protected AAC formats, no quality is gained by doing so, and in fact some quality may actually be lost in the process. See our April 19, 2007 column on transcoding lossy formats for more information on this.