I get the same errors... security.ubuntu.com, medibuntu, dropbox, etc.
It's not the same one each time though. This is occurring for me on
several different machines (both 32 bit and 64 and even on one netbook
edition). I also concur that everything seems to update fine until you
add a third party repository... Then these "wicked" errors begin. I'd be
glad to provide more information if needed.

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Apt has strange network errors when updating indexes.
https://bugs.launchpad.net/bugs/574886
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