Windows – Use the same port (443) for hosting multiple applications

httpsopenvpntcpwindows

I have a Windows Server. I am hosting multiple websites on port 443 using the Host Header Binding in IIS. This works great, however, I am looking for a solution to somehow be able to use port 443 to run an OpenVPN server on the same windows machine.

Is there some way I can use IIS to bind a vpn.example.com port to 443 and make it route all incoming connections to an internal port, e.g 8080, which will host the OpenVPN application, or does anyone know of a possible application/workaround that will accomplish the same thing?

Best Answer

Not possible.

Making OpenVPN use port 443 is possible and an useful way of bypassing a firewall that has port 443 open. That's because both HTTPS and OpenVPN uses TLS encryption, making it almost* impossible to distinguish one from another.

However, while OpenVPN utilizes the common TLS encryption, it doesn't implement HTTP protocol; the one having the Host: header allowing the name based virtual hosts. Therefore, you'll need another IP address for your OpenVPN server.

(*) Some deep packet inspection may have ability to detect patterns that doesn't match HTTPS.

Related Solutions

IIS URL Rewrite HTTP to HTTPS with Port

Even though the question was answered awhile ago, this is the rule that I used.

<rule name="Redirect to HTTP on different port" enabled="true" stopProcessing="true">
      <match url="(.*)"/>
      <conditions>
        <add input="{HTTPS}" pattern="ON"/>
      </conditions>
      <!-- Cannot Use {HTTP_HOST} as it contains both the {SERVER_NAME}{SERVER_PORT} -->
      <action type="Redirect" url="http://{SERVER_NAME}:1000{HTTP_URL}" redirectType="Found" appendQueryString="false"/>
    </rule>

Iis – How to run VisualSVN Server on port 443 running IIS on same server

Already answered there. Use the following command:

netsh http add iplisten ipaddress=x.x.x.39

Best Answer

Related Solutions

IIS URL Rewrite HTTP to HTTPS with Port

Iis – How to run VisualSVN Server on port 443 running IIS on same server

Related Topic