Reply #5: yes, but it violates your term of service agreement.

[northzax]

there is software out there (go find it on google, if you wish) that will break iTunes' prohibiton on downloading from the iPod. It will make the song folder on your iPod viewable, from which you can copy the songs to your hard drive and import them into iTunes. Note that any song purchased from iTunes will not be playablw without the owner's password.