Q: I am unable to rip tracks from my iTunes library to my iPod. I can copy and drag tracks from the library to my iPod under devices, but nothing happens when I do this—I do not get a plus sign when I hover over my iPod and no copying takes place. This is driving me crazy. Please can you help me?
A: The first thing to do is to ensure that your iPod actually is set for manual management from iTunes. You cannot drag and drop content to an iPod that is set to use automatic synchronization.
To check this, connect your iPod to your computer and then select it from the iTunes Devices listing at the left-hand side of your iTunes window. On the main “Summary” screen which appears, ensure that the box for “Manually manage music and videos” is checked:
If you are in fact in manual mode (the box is checked) and you still cannot drag-and-drop tracks onto your iPod, ensure that the files themselves are actually accessible. The simplest way to do this is to attempt to play the track in question. If you have tracks stored on an external hard drive or a network location that iTunes cannot currently access, you naturally will not be able to transfer these tracks onto your iPod.
If you are using an older version of iTunes 7, you may also need to expand the iPod content in your Devices listing by clicking the small triangle which appears to the left to display the categories and playlists on your iPod. Once you’ve done this, try dragging and dropping your items directly onto the “Music” section. Note, however, that this issue was fixed in later versions of iTunes, and is not a problem in iTunes 8, so if you are using an older version this may be a good reason to upgrade to something more current.