Trying to sync ipod using windows media

Question

I have recently bought a new ipod nano and when i first plugged it in, it automatically added my songs from my windows media. After creating my itunes account, i cannot seem to retrieve any songs from my windows media. It worked the first time, but any new songs added to my media will not Sync. Any help would be appreciated.

Answer 1

I made a similar mistake when I bought my first iPod. I begrudgingly resigned myself to the fact that any and all synchronization with my iPod MUST be done with iTunes if I wanted to get the full functionality out of my iPod. My suggestion at this point would be to open iTunes, sync your iPod and then choose restore. It will take your iPod back to the way it was when you originally purchased it. Once this process is done, sync only with iTunes.
The problem here is the way iTunes stores the files versus the way Windows Media Player stores them. For iTunes, it creates a crazy file storage and naming structure. It also has several files containing such things as playlist and player content. Windows Media Player simply copies file and folder structures of the selected files. It essentially treats the player as if it were any other storage device. While easier for someone to just drag and drop new stuff to the player, the iPod doesn't recognize any of the copied files like other brands do.
A strange side-effect of the crazy naming structure is that if you drag and drop files to your iPod or use WMP sync, not only does the iPod not recognize them, they still take up room. So, your iPod can appear to be full to iTunes. This can be frustrating if you expect the iTunes sync to clear out any unwanted files. Windows Media Player will also not recognize and delete the files added by iTunes.