My 3gs wont sync certain songs from itunes

does anyone know what is going on?  i make playlisys for my 3GS to sync.  for instance, my most recent playlist had 38 songs on it but my phone and itunes only synced 27 of the songs.  if i try and drag the ones that didnt make it in individually, nothing happens...very annoying!!! help!!!

It means that itunes on your computer cannot find where the songs are on your computer.  what you do is right click a song in itunes when you are in your library and then click on find

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