Q: Hi, I am in a quandary. I have two computers in different states with iTunes on both which necessitated manually managing my music. My iPod will not transfer the music back; when I drag the tune over it won’t do anything. Will my tunes on the iPod be lost if I switch back to Auto Sync? What am I doing wrong? I am so technology challenged.
A: Unfortunately, iTunes does not allow you to copy music from your iPod back to your computer. The only exception to this is items purchased from the iTunes Store, but even this is an “all-or-nothing” transfer – you can’t select specific items.
To transfer content from your iPod back to your computer, you will need to look at third-party software. Our iPod 201 article, Copying Content from your iPod to your Computer describes how to do this and lists several software packages for this purpose.
Another possible option is to sync the two iTunes libraries themselves so that they contain the same content, and then choose to automatically sync the iPod to the new consolidated library. There are several third-party software applications that can be used to sync iTunes libraries, but if you’re using iTunes 9, the new “Home Sharing” feature can assist you with this directly, without the need for any third-party software. Home Sharing allows you to sync up your iTunes libraries between multiple computers on the same home network.
Note that switching your iPod to automatic sync in this situation would definitely be a bad idea, since this would replace all of the content that is currently on your iPod with the content in the current iTunes library, erasing anything that was on the iPod but not in iTunes. Before doing this you should definitely ensure that you get a single consistent library in place containing all of the tracks that you want to keep on your iPod.