Hi Everyone, Setting up a reverse caching proxy with Squid on windows 2003 (unfortunately) in a lab for a proof of concept. Using 2.7.STABLE8. Never done this on windows so be kind. The reverse proxy works to any of the sites on the webserver, but if I turn off the webserver and attempt to get to the sites via the proxy's cache it times out (to test a failure of the webserver). I have a separate Squid reverse proxy and a separate IIS6 web server running an application called Umbraco. I have done a fair bit of googling but can't find the answer, I mainly have used the guides below as well as a bit from the squid documentation. http://ashleyangell.com/2009/03/configuring-a-basic-reverse-proxy-in-squid-on-windows-website-accelerator/ http://www.mnot.net/blog/2007/12/12/stale http://www.howtoforge.com/how-to-set-up-a-caching-reverse-proxy-with-squid-2.6-on-debian-etch Here are the two squid.conf's I have tried (mashed together from my meagre knowledge and the above): http://pastebin.com/L9EjafJW http://pastebin.com/QS6kxUwN I have also played with the cache control setting in IIS, but it doesn't appear right (two Cache-control entries?), I get the below if I wget the index on the webserver Server: Microsoft-IIS/6.0 X-Powered-By: ASP.NET Cache-Control: public, max-age=5,stale-while-revalidate=600, stale-if-error=36000 Set-Cookie: ASP.NET_SessionId=fdlkjayuf98dsfgnkjdsl7; path=/; HttpOnly Cache-Control: private I have tried this via the suggestion here, http://support.microsoft.com/kb/247404 which edits the IIS metabase to add the CacheControlCustom entry, but this doesn't seem to change the headers. So I added a custom header to the site which is what gives the dual cache-control entries in the header. Could this be to do with IIS using http:1.1 by default? I tried setting both HcNoCompressionForHttp10 and HcNoCompressionForProxies to FALSE as someone did here http://objectmix.com/inetserver/285880-compression-disabling-transfer-encoding-chunks.html to no avail. I know this is a long shot but anyone got any ideas as to why it isn't caching the site, it could be a simple config file snafu that someone more knowledgeable in Squid will pickup pretty quick.