iPod Songs Won't Transferby Laurel Storm
When syncing your music to your iPod, you may run into unexpected issues, especially if your music library is vast, comes from multiple different sources and spans many years of collecting. There can be several different reasons why certain songs won't copy to your iPod; the method you have to use to solve the issue varies depending on what exactly the issue entails.
If you have purchased music from the iTunes store using two different accounts, your computer may not be authorized for one of them, causing you to be unable to play songs bought with that account or copy them to your iPod. To solve the issue, click "Store," select "Authorize This Computer," enter the Apple ID and password associated with that specific account and click "Authorize." If the issue persists, you may need to perform the authorization using an administrator account or delete a folder called "SC Info." Refer to the help files on Apple's website (see Resources) for more information.
Some of the files in your music library might play with no issues in iTunes but, at the same time, be incompatible with your iPod. If this is the case, the files won't copy unless you convert them to a compatible format. Open the iTunes preferences, select "General" and click "Import Settings." Depending on your preference, select the MP3, AAC or Apple Lossless encoder using the "Import Using" drop-down menu. Click "OK" to save your changes and then click "OK" again to close the Preferences window. Locate the problematic songs in your library, right-click each of them and select "Create MP3 Version," "Create AAC Version" or "Create Apple Lossless Version" depending on the encoder you chose. Once the song has been converted, remove the old version from your iTunes library.
While reorganizing your hard drive, you may have accidentally moved or renamed sound files associated with your iTunes library. If this has happened, iTunes will be unable to copy those songs to your iPod. You can fix this issue in two different ways. If you preferred having the files in their original location, move them back and rename them to their original name. If you would rather have the files in their new location, delete the entries for the problematic songs from your iTunes library and then add them again.
From iTunes 11 onwards, any songs you may have bought from the iTunes Store and then deleted from your hard drive are still displayed in your library. If you then attempt sync your iPod, you will be unable to copy these songs to it and receive an error message. To fix the issue, switch to the "Music" tab of iTunes, right-click on any column header and ensure "ICloud Download" is selected. Click on the "Cloud" header to bring all songs that exist only on iCloud to the top of your library and then click the download icon in the "Cloud" column to download each individual song.