Cannot sync song from iTunes playlist to iPod Classic

I haven't been able to sync a song from one of my playlists in iTunes to my iPod ever since I've updated from earlier programs. The song was added to the playlist manually, but that never mattered before. If I can't clear this up I'm afraid my iPod is useless!

You could try creating a new playlist from that one. Select the complete Playlist and then select New Playlist from selection. In my screenshot, I right-clicked to get this pop-up menu, your iTunes may look slightly different, but the choice will be there somewhere (try the + icon in the bottom left of the iTunes window).
Once you have created the new Playlist, try Syncing that to your iPod. If only that song is missing, that suggests there is something wrong with the song that prevents it going onto your iPod. But if the complete (new) Playlist fails to transfer, then that suggests that something is wrong with your Sync preferences.

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    http://support.apple.com/en-us/HT204084
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    If any post helps or solves your issue, please mark it that way accordingly. Thank you for helping the boards!

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