After many hours of verifying certificates in Keychain and testing with roles that required a client side certificate failing. I finally found the resolution to my problem. You have to create an identity preference mapping in Keychain so that way the client side cert would be presented correctly to the Juniper SSL IVE. I wanted to share the link to this article with anyone else that is trying to do certificate checks and Mac clients. The article is here: http://support.apple.com/kb/HT1679 ... View more