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I've got a Squid proxy server using the sslbump feature that works fine with self-signed certs, but the browsers complain about it. Now I'm trying to setup the Squid server as a subordinate CA of our Active Directory CA so that the browsers trust the certs created by Squid. Here's an overview of what I'm doing that's not working:

  • Creating a CSR with openssl on the squid server
  • pasting that CSR into Microsoft AD Certicicate Services (using the Subordinate CA template)
  • Taking the resulting Base-64 cert and putting it on the Squid server

This results in the browsers complaining about the certs. When I view the cert from within the browser I always get the following error: "Windows does not have enough information to verify this certificate", and there are no CAs in the certification path. The steps I listed above are in greater detail here. Certs aren't my strong point, and I'm not sure where to go from here. I feel like the issue might be related to how I created the CSR, or possibly that my understanding of the process is fundamentally wrong. Any help is appreciated.

And yes, our end users are aware of this.

  • The cert Squid is using is PEM format and has two concatenated certs, but when I download the cert file the browser received, it only contains one cert. Is that normal? – bcst Oct 25 '16 at 20:22
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The answer may be late but anyway - you need to cat private key and subordinate certificate that you got from your Enterprise CA together to make a pem out of it that can be used in ssl-bump's cert= directive.

More info at https://blog.diladele.com/2017/03/21/using-subordinate-ca-for-https-decryption-in-active-directory-integrated-squid/

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