Cannot transfer songs to iPod from iTunes.

Please help. I can download songs to my iTunes but the iPod will not update when plugged in. It tells me that it has but when I go to my iPod the songs are not there. I have 3 cds that I have recently downloaded that will not upload to my iPod. Everytime I plug my pod into the computer it tells me that it is updating these 3 albums onto the pod but it doesn't. I tried several times and I got the same thing everytime. Looking at my songs on my iPod from my iTunes it shows these albums are there and play from iTunes but when I try searching from the actual iPod they are not. Oh and everything is updated and I have "Automatically update all songs and playlists" button selected in my ipod options!

I have the SAME problem. "Updates successful" message followed by missing songs on the iPod and next update attempting to transfer these songs all over again. Tried everything, including "strange iPod behavior" suggestions to no avail. This has started since the January installation of the new iPod Updater.
Please help.....
  Windows XP   20GB iPod

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