Q: My daughter has a iPod nano. She will connect her iPod to my iTunes and drag and drop songs from my library to her iPod. However, when I try to do the same the song will display a circle with a line through it indicating that this can’t be done. She goes to her girlfriend’s house and obtains music in this manner as well. I have the latest software updates from Apple. Why isn’t this working for my iPod?
A: Your daughter is likely using her iPod in “manual” mode whereas you have your setup to automatically sync content fro. your iTunes library. These two options are mutually exclusive, since if you are choosing to manage the content on your iPod manually, iTunes will never sync any of that music or video content to your iPod automatically—you must add it all manually. On the other hand, if you’re using automatic synchronization, adding content manually doesn’t make sense, as the content should already be synced from your iTunes library automatically. If you’re syncing only selected playlists, you would simply add any tracks that you want on your iPod to the playlists that you’re already syncing to your iPod.
To switch your iPod into manual mode, simply connect your iPod to your computer and select it from the Devies list on the left-hand side of your iTunes window. From the “Summary” screen which appears, look for the option, Manually manage my music and videos
Checking this option and clicking the “Apply” button will switch your iPod into manual mode, and you will then be able to add content to it via drag-and-drop. In manual mode, you can also manage the content directly on the iPod itself through iTunes by clicking on the small triangle to the left of your iPod in the Devices listing and expanding it to show the content on the iPod itself.
From there, you can navigate through it in iTunes as if it were a separate iTunes library, including updating any existing tracks on your iPod or removing tracks from your iPod.