Can't copy some songs onto ipod

Some of my songs won't copy onto my ipod nano for some reason, even though I have the new version and enough space on my ipod, and the files are all fine. I can't figure out why some songs are unable to be imported...(no warning sign, I only find out when I can't find the song I want on my ipod)
The only way I can get the songs onto my ipod is to put them in a playlist and then load the playlist into my ipod. Only then are the songs imported into the ipod.
Does anyone know what the problem is, or how I can make itunes copy ALL my music into my ipod without creating a separate playlist? This only started happening recently, everything worked fine before!
Thanks!

Same problem. Some of my playlists wont import either. HELP

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