John,
        I believe what you need to do is export the Certificates from the IIS 
servers, they will be saved in a .pfx file, which is the PKCS12 format.  
OpenSSL can convert these into the PEM format that squid supports, these 
commands will give you the desired output.

Exports the Certificate:
openssl pkcs12 -in server.pfx -out server.crt -nodes -nokeys -clcerts

Exports the Private Key (Note will not be encrypted, store in safe place):
openssl pkcs12 -in server.pfx -out server.key -nodes -nocerts -clcerts

The openssl man page and the pkcs12 man page will have more information about 
these options if you need them.

Thanks,
     Dean Weimer
     Network Administrator
     Orscheln Management Co

> -----Original Message-----
> From: John Gardner [mailto:john.gard...@southtyneside.gov.uk]
> Sent: Sunday, February 13, 2011 2:13 AM
> To: squid-users@squid-cache.org
> Subject: [squid-users] Reverse Proxy and Externally Generated Wildcard SSL
> Certificates
> 
> Hi everyone.  I've got a query about running Squid as a Reverse Proxy that I
> hope someone can answer.
> 
> Over the past year, I've been tasked with introducing serveral Squid servers
> into our organisation, most of them so far have been internal Caching
> proxies, but I'm now at the stage where I need to implement a Reverse
> Proxy (RP) in our DMZ.
> 
> We're going to offload the SSL onto the RP using a Wildcard SSL Certificate
> and during testing I used the advice here: http://wiki.squid-
> cache.org/ConfigExamples/Reverse/SslWithWildcardCertifiate.  This was
> great to test everything and worked well.  However, now I'm ready to put
> this into a Production environment and I have to deal with the fact that we
> are fundamentally a Windows house.
> 
> They have already procured wildcard SSL certificates from Verisign, where
> the original CSR was generated on a Windows server sent off to the CA
> (Verisign) and then then the wildcard certificate returned to us.  My question
> is quite simple, how do I import the wildcard certificate into openssl on the
> RP server?  All the examples I've seen online assume that you're generating
> the CSR on the proxy server itself but I don't have that luxury unfortunately.
> 
> I know this is more of an OpenSSL question rather than pure Squid question,
> I was just hoping that someone on the list has already done this and can give
> me some advice.
> 
> Thanks in advance.
> 
> John
> 
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