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I'll do my best to explain this.

I've got a Windows 2008 server with TWO local intranet-sites running on it.

The first website will open if you just type in the name of the IP address - 192.168.1.64.

I set the second website up on port 85. So if you go to the IP addresss 192.168.1.64:85, it will open the second website. I had our IT department create a subdomain on our local intranet, connect.placeholder.net, and asked them to set it to the IP address and port of the second website. They said that it wasn't possible to include the port, that I would have to use connect.placeholder.net:85 to get to the correct site.

So, I've spent the entire day, playing around in IIS trying to find a way to forward this incoming traffic to the correct port.

Any ideas?

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It is a virtual hosting configuration that you need, not a port forwarding one (unless you also use HTTPS). However, I don't know about IIS configuration. –  Tonin Apr 1 '13 at 17:11
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2 Answers 2

Change the port on the second web site to port 80 and then configure host headers for each web site for the appropriate name.

http://technet.microsoft.com/en-us/library/cc753195(v=ws.10).aspx

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Bingo! I had it setup exactly like this, but couldn't get it to work - except I was using a different port number. I changed it back to default, and boom, worked perfectly. Thanks so much. –  Josh Apr 1 '13 at 20:34
    
Glad to help... –  joeqwerty Apr 1 '13 at 21:51
    
@Josh Don't forget to upvote this answer and mark it as correct for the benefit of future readers. –  Wesley Apr 2 '13 at 0:11
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As long as the websites are non-HTTPS and both websites are hosted on the same server, simply tell IIS to use virtual host names (vhost), this will remove the need for separate ports for each site. If they are encrypted, you'll need either separate IP addresses (i.e., 1 for each site) or a wildcard SSL certificate and vhosts.

If the websites are not hosted on the same server, in order to use a subdomain you'll either need a separate IP address for the second website and DNAT port 80 and/or 443 at the router, or have IIS on the first server act as a proxy for the second.

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