[plug] Getting SQUID to play nice with windows updates

[Mark Slatem]

Hey all,

This week I have been spending some time dabbling with a squid test 
server. I have setup squid as a transparent proxy and have the firewall 
redirect all http requests to the squid box, then on the squid box I am 
using iptables rules to redirect port 80 >> 3128

This is all working well but I am having major problems getting "windows 
updates" to be cached and reserved to windows clients on the LAN. There 
does not seem to be any definitive information on the net about this, 
but from what I have read Microsoft keep changing their settings and now 
specifically send messages to proxy servers requesting updates to not 
cache, and also they will change the data of update files while 
retaining the file names, this also causes major problems if you tell 
squid to cache all update content regardless and then it serves 
incorrect or  stales versions of updates to clients.

Since this is one of the reasons we want to deploy squid in lan 
environments, I was wondering if any of you would like to share your 
pearls of wisdom on if and how you overcame these challenges, and if in 
fact it is possible to get this working reliably using squid.

Thanks

Mark