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I am currently trying to set up a network with both a secure webserver and an internal openvpn server. The webserver is running windows 2008 and the vpn network is running the Access server from OpenVPN. The problem that i'm having is that I want to be able to access both servers from outside the NAT. I would like to do something like this:

                    Outside
                       |
                       |
                      NAT
                       |
           ------------------------------------
           |                |                  |
        test.org           vpn.test.org       dns.test.org

and host test.org and vpn.test.org on different machines. I want both to be accessible from port 433 and from the outside. I'm not sure how to go about doing this so any help would be greatly appreciated.

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Do you have multiple public IP addresses pointing to the NAT? –  ghm1014 Jul 11 '11 at 19:29
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1 Answer

up vote 6 down vote accepted

If you need them both to be available on port 443, you'll need two IP addresses on the WAN interface of your NAT device.

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4  
DNS only resolves names to an IP address, it has nothing to do with port numbers. –  EEAA Jul 11 '11 at 19:21
1  
Well technically yes, you could set those two DNS names resolve to the internal addresses of the hosts, but that's not going to satisfy your requirement that they be accessible from the outside. –  EEAA Jul 11 '11 at 19:24
3  
Once again, DNS has zero control over port numbers. No, it's not possible. –  EEAA Jul 11 '11 at 19:26
2  
Assuming that you're running SSL over port 443, everything is encrypted. How would you suppose you'd be able to tell where traffic should be routed? –  EEAA Jul 11 '11 at 19:30
1  
@bkrupa - if the traffic were not encrypted, and if you and some sort of intelligent proxy you could possibly do something like this. Neither of those are true in your case, though. –  EEAA Jul 11 '11 at 19:33
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