nope... works on unjailbroken too. the guys at mediamonkey reverse engineered the ipod database structure, so they can index the files just like iTunes. Any program can write to an ipod/iphone, but only a couple can write the file AND make the database entries valid so that the device sees the files. there was a little downtime when apple changed the DB structure when they included ebooks (iOS3 to iOS4), but they sorted that out too. You can now upload videos, books and music using MediaMonkey.