5797 Views 4 Replies Latest reply: May 24, 2009 1:06 PM by maf20
With some exceptions, such as songs purchased from the iTunes Store and data like play count and ratings, iTunes syncs from computer (the iTunes library) to iPod and NOT from iPod to computer. It's an intentional design choice by Apple. If you sync the iPod to your new iTunes music library, your iPod's current contents will be erase.
However, there are third-party utilities that can transfer song files from iPod to computer, and some are free, for example
I have used this utility successfully, but it is not free
You can also use this method below to transfer songs off the iPod without using any utility.
After you have safely transferred the song files off the iPod, you can add those songs to your new iTunes music library, and sync everything to your iPod.
Although the iTunes Store no longer uses DRM on its songs, older purchases had DRM. To play those songs on a computer, it must be authorized with your iTunes Store account. To do so, in iTunes
menu bar -> Store -> Authorize Computer
and provide the user name and password of the iTunes Store account used to purchase those songs.
You can have up to five computers authorized with one iTunes Store account. If you ever reach that limit because you forgot to deauthorize old computers that you no longer use, you can deauthorize them ALL and start over, by going to your +Account Summary+ in iTunes (go to the iTunes Store view and click on your user name at the upper right corner). This command will not be there unless you have reach the limit of five.