Q: My boyfriend and his male dog moved in. Male dog urinated on my PC and killed it (the PC, not the dog). The PC had my entire music library on it. I have a laptop and I’ve set up iTunes on it in hopes of recovering my 1,689 songs that are on my iPod. Well, it transferred my purchased songs (836) but how the heck do I get the other songs onto my laptop? My other major issue is that I purchased some songs from iTunes yesterday and they won’t sync onto my iPod classic, but they did sync onto my daughter’s nano.
A: In an attempt to combat piracy, iTunes only allows you to transfer songs from your iPod to your computer that were purchased from the iTunes Store with the same account as you’re using on your computer. To transfer the other music back you will need to use a third-party iPod transfer utility. You can find more information about these in our tutorial on Copying Content from your iPod to your Computer. As this is a one-time thing, you’re best to look at a free solution such as SharePod.
In terms of syncing purchased songs onto your iPod classic, ensure that your iPod classic is set to either automatically sync all tracks from your library, or if you are syncing selected playlists only, ensure that you have put those tracks in the appropriate playlist(s). You can find these settings under the “Music” screen in your iPod settings in iTunes. Alternatively, in the current version of iTunes you can also simply drag-and-drop those tracks onto your iPod from your iTunes library, even if you’re otherwise managing its content automatically. Manually-added tracks will be copied to your iPod and will appear listed in a section on the “Music” screen below your automatic sync settings.
If the tracks are still refusing to transfer and iTunes is not displaying any warning messages, try right-clicking on your iPod and choosing the “Reset Warnings” option. This should at least ensure that iTunes tells you why it can’t transfer these tracks, which may help you to isolate the problem.