After thorough research I have come to ask for assistance. What I want is to create a configuration similar to what Apache/Tomcat have with I believe AJP only Apache to IIS. I know due to TLS, IIS, x509, it is generally difficult as what I am wanting to do creates a MITM (Man-In-The-Middle) Internet ==> Apache Reverse Proxy === IIS backend Authentication Client certificate I know the reason right now I am losing the header information on IIS is due to the TLS session ending after I hit my proxy server. I thought by configuring my virtual host utilizing SSLCACertificateFile it may work however I still receive the 403.7 (IIS). I was hoping to leverage mod_proxy parameters that I leverage with tomcat would work with IIS but I am having no success. My <virtual host> is using the following so far SSLEngine On SSLVerifyCLient require SSLVerifyDepth 4 SSLCertificateFile ssl.crt/cert.pem SSLCertificateKeyFile ssl.crt/key.key SSLCACertficateFile ssl.crt/CAbundle.pem SSLOptions +ExportCertData SSLProxyEngine On JkMount / JKMount / ProxyRequests Off ProxyPreserveHost On ProxyPass /location/ "url:7443" My goal was to build this <virtualHost> to where I have Apache Reverse Proxy working with both Tomcat and IIS on the backend both accepting client certificate login. The other approach I am looking into is attempting to see what header information occurs between apache and IIS and is there anyway to configure IIS to leverage x509 http syntax to grab the information and leverage that for authentication. I need to leverage HTTP and not HTTPS and capture that traffic with wireshark to see if there is anything there to work with. This is my debacle I am currently working through and appreciate any assistance.