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Apache Reverse Proxy to IIS TLS/Client certificate authentication debacle


Apache proxy: passing on REMOTE_USER to backend serverConfiguring client certificate authentication in apacheReverse Proxy Server SSL?Certificate Authentication from Salesforce.com through a reverse proxyTomcat two way SSL with APR loses client certificate after a few requestsBasic auth Apache with TomcatIIS enable authentication for reverse proxyIs it possible to configure IIS with the `optional_no_ca` option for the client certificate validation?Client sends TCP ACK FIN right after successful TLS HandshakeIIS 10 ARR : Client certificate not interpreted by backend server






.everyoneloves__top-leaderboard:empty,.everyoneloves__mid-leaderboard:empty,.everyoneloves__bot-mid-leaderboard:empty margin-bottom:0;








0















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, it is generally difficult as what I am wanting to do creates a MITM (Man-In-The-Middle) exploit. Expecting IIS to approve the authentication sent from the apache server without executing its own handshake.



Internet ==> Apache Reverse Proxy === IIS backend
Authentication Client certificate



I thought by configuring my virtual host (via my Apache reverse proxy) 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 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/ http://ip:7443


My goal was to build this 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 see what I can capture with HTTP and 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.










share|improve this question




























    0















    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, it is generally difficult as what I am wanting to do creates a MITM (Man-In-The-Middle) exploit. Expecting IIS to approve the authentication sent from the apache server without executing its own handshake.



    Internet ==> Apache Reverse Proxy === IIS backend
    Authentication Client certificate



    I thought by configuring my virtual host (via my Apache reverse proxy) 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 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/ http://ip:7443


    My goal was to build this 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 see what I can capture with HTTP and 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.










    share|improve this question
























      0












      0








      0








      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, it is generally difficult as what I am wanting to do creates a MITM (Man-In-The-Middle) exploit. Expecting IIS to approve the authentication sent from the apache server without executing its own handshake.



      Internet ==> Apache Reverse Proxy === IIS backend
      Authentication Client certificate



      I thought by configuring my virtual host (via my Apache reverse proxy) 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 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/ http://ip:7443


      My goal was to build this 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 see what I can capture with HTTP and 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.










      share|improve this question














      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, it is generally difficult as what I am wanting to do creates a MITM (Man-In-The-Middle) exploit. Expecting IIS to approve the authentication sent from the apache server without executing its own handshake.



      Internet ==> Apache Reverse Proxy === IIS backend
      Authentication Client certificate



      I thought by configuring my virtual host (via my Apache reverse proxy) 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 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/ http://ip:7443


      My goal was to build this 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 see what I can capture with HTTP and 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.







      iis apache-2.4 proxy authentication certificate






      share|improve this question













      share|improve this question











      share|improve this question




      share|improve this question










      asked Jun 7 at 18:38









      JessayJessay

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