troubleshooting Question

Access Two Sub-domains on Different Servers using only one IP Address

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Apache Web ServerMicrosoft IIS Web ServerDNS
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I have a dilemma which I hope the community can help me resolve. I have created two sub-domains and each will be hosted on different servers. Internally I have no problem connecting to either one.

The problem is when I try to connect from outside our network. We have a single IP address with multiple web servers in-house. I have tried using host headers with redirect to no avail. I tried setting up virtual hosts with redirect, also no go. If at all possible, I would like to avoid having to use specific ports for each site.

Internal DNS obviously works. Externally, I pointed both sub-domains to our IP address.

Main site ( = IIS6
Sub1 ( = LAMP server hosting WordPress blog
Sub2 ( = custom app server

What am I doing wrong? I know I'm missing some piece of the puzzle.

Thank you.
IT Manager

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