Thanks for your bugreport.
This sounds like something with your local proxy (apt-cacher?) is wrong.
I convert this to a question.
** Changed in: update-manager (Ubuntu)
Status: New => Invalid
** Converted to question:
https://answers.edge.launchpad.net/ubuntu/+source/update-manager/+question/69242
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Error in Upgrading from Intrepid to Jaunty(Desktop)
https://bugs.launchpad.net/bugs/368569
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