Q: I just got a new iPod classic and I’m trying to upload content onto it. It’s working but when I try to upload a movie, I check “Sync Movies” and then a box appears that says: Are you sure you want to sync movies? All existing Songs, Movies and TV shows on the iPod will be removed and replaced with movies from your iTunes libary. How do I upload movies without having to remove all existing songs and movies?
A: The most likely cause of this is that you have been transferring music to your iPod manually, so it is not already in any kind of automatic synchronization mode. This warning is advising you that to transfer movies on using automatic synchronization, you must set iTunes to synchronize all content to your iPod automatically.
Essentially, confirming that you want to do this will set iTunes to automatically synchronize your music and video content to your iPod. This will replace everything that is presently on your iPod with content from your iTunes library. Of course, if the content in your iPod is still in your iTunes library, then switching to automatic synchronization is really not an issue, as iTunes will simply go through the library and retransfer the same content back again (in reality, it will probably recognize most of the content and simply match it up, rather than retransferring it).
If, on the other hand, you’ve been using manual mode to transfer music to your iPod and remove it from your iTunes library, or you have another reason for wanting to use manual mode, then you will need to transfer your video content in the same way—by dragging and dropping it onto your iPod. In this case, leave the “Sync Movies” checkbox OFF in iTunes, and just take items from within your “Movies” folder in iTunes and drag them onto your iPod in the same way that you transfer your music..