Q: I’m having trouble creating playlists. I click the plus sign (+) in the bottom left corner of the iTunes window, enter a new title, and drag songs from the music library to the new playlist. When I click on the playlist the selections I put there show up fine. However, they never show up on my iPod. After doing all of the above I sync, but the playlist never shows up on the iPod under Playlist? What do I do?
A: The most likely cause of this is that your iPod has been set to sync only selected playlists. In this mode, any new playlists you create are not automatically synced to your iPod—you must specifically enable them for syncing.
You can check your iPod synchronization settings by connecting your iPod to iTunes, selecting it from the Devices list on the left-hand side of the iTunes window, and then choosing the “Music” tab on the main screen:
This will indicate whether you are synchronizing ALL playlists or only selected playlists. Syncing selected playlists is generally used to limit the content which you sync to your iPod, most commonly due to space restrictions (ie, your iTunes library is larger than your iPod’s capacity). If this is not what you desire, however, you can easily select “All Songs and Playlists” and click the “Apply” button to simply tell iTunes to transfer everything in your iTunes library (including all playlists) onto your iPod. Note that if you do not have sufficient space on your iPod to store your entire iTunes library, iTunes will give you an error message advising you of this and offering to help free up space on your iPod by removing certain types of content such as podcasts or photos.
If you are synchronizing only selected playlists, simply ensure that any new playlists you have created which you would like to have on your iPod are selected on this screen and click the “Apply” button. The new playlists will be transferred to your iPod, along with any content listed in them which is not already on your iPod.
Keep in mind as well that some of the newer iPod models such as the iPod nano (with video) and iPod classic now support playlist folders, so even if you are synchronizing your new playlists to your iPod, they may be shown in a sub-folder rather than on the main iPod playlist screen.