ITunes 7.0.2 synching with video iPod

After upgrading to iTunes 7.0.2, I placed my iPod video into the dock. A message came up stating that not all of my files had been transferred because my iPod software was too old. This meant that all my purchased songs and videos did not copy over. I know I have the latest software edition for my iPod and the Update button is not available to even check for updates.
Now the interesting thing is when I place the iPod into the dock while the my iMac is off and then boot it up, it syncs correctly with my iPod. All purchased material copies over and no error message comes up. It is only when I try to insert the iPod while the iMac is running I have the problem.
Any ideas from anyone?
D

Yes, Quicktime is up to date. Everything is up to day, but when placing the iPod in the dock while the iMac is running is when the problem arises.

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