Ipod will not update new songs from itunes

My ipod will not update new songs from itunes. I've purchased several songs from the music store, updated my playlists and as added some from my CD collection and they are not transfering from my library to my ipod.
I've tried numerous configurations under the preferences - ipod menue but still can't get them to transfer.
One error I occasionally get is "ipod cannot be updated because there is not enough free space to hold all of the songs in the itunes music library"
There is plenty of room on my ipod so I can't figure out why. It almost seems as if it is trying to copy all of my songs not just the new ones because all songs in my librbary are checked.

Thank you for responding.
Doesn't it have to be on either manual or auto update? What other option is there?
I will try downloading latest updates.
I know it will work if I reset it (have done it a few times already). I just hate having to restore factory settings everytime I want to put a new song onthe ipod.

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