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That describes the function of the Squid Proxy. Once the first person has obtained an update through the proxy, then it will be cached for future downloads.
Are you wanting to know what configuration changes are needed on the Windows machines to use the proxy? If so you are posting in the wrong forums. If you go to the Microsoft web site and search for "proxy windows update" (or knowledge base 900935) you should be able to find the answer, which differs depending upon how you want to get the updates.
I have been using squid cache for a while now and it caches most of the files the way it should, except for windows update files. I run squid transparently so I dont have to bother about configurations on user computers.
Was thinking someone here has found a way of caching those.
I have seen a number of answers to this but they dont appear to work.
I beleive Caching WU can work (legally) coz the WGA validation process does not require or collect any information that could personally identify you. Customers who have a genuine copy of Windows and who decide not to complete the validation process can still obtain critical software updates by using the Automatic Updates feature.
The Automatic Updates feature is NOT affected by the WGA validation check. Therefore, one can use the Automatic Updates feature to receive critical Windows updates. NOW, those are the ones I want to be caching.
Now, when I tail squid's access log, I can see download of those taking place (even to some computer owners who dont know what WGA is all about).
It's certainly possible and legal to perform distributed Windows Updates, as this is how WSUS works. We have a seperate (Windows) WSUS server which downloads the updates one, and which the other machines then get their updates from. The WSUS server goes direct so we don't actually use the proxies for any of our Windows Updates.
This is done using a Windows server, although as far as I know it just uses http transfers. I don't expect anyone has created a linux equivelant of a server that is just designed to serve to Windows machines.
Back to squid - assuming that there is no session information, and that the transfers don't have don't cache option set (I wouldn't expect eithr of these being the case), the other things you may want to check is your: maximum_object_size and how big your cache is allowed to be, as either of those could stop files from being cached.