Windows update tells proxy servers not to cache its downloads. To get round this in squid, add the following to your acls:
acl windowsupdate dstdomain .windowsupdate.com never_direct allow windowsupdate
never_direct tells squid to always try to get the object from cache even if the client specifically asks for it.
UPDATE: I found that Microsoft change the updates whilst keeping the old filename, and this will break if you cache the files. So the best solution is to use SUS (Broken link ~~http://microsoft.com/sus/~~).
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