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2 web sites on different IP addresses (both must be SSL) 1 server that is publicly accessible via 2 different IP addresses.

I want to routing to be as follows:
<External IP 1>:443 --> :443
<External IP 2>:443 --> :443

I am having trouble figuring this out. Apparently it is only allowing for unique ports, even though the external IP addresses are on separate interfaces.

Any ideas would be helpful.

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To be perfectly clear, what you'd be doing is not "routing" but "binding."

It doesn't sound like you've actually configured two different sites in IIS. If this is the case, you have to make a new site using IIS Manager. Point that new site to the second site's files, set up the application pool (if applicable), configure SSL, and set the IP/protocol (which would be External IP 2, port 443) binding for the second site.

As an aside, you probably want to set up redirection from external IP/URL:80 to external IP/URL:443. Your website/application probably doesn't care if your users are authenticating unencrypted, so you have to set IIS to do this.

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The "Advanced..." button on the "Web Site" tab of the web site's properties sheet will allow you to specify a unique IP/port combination for each web site. IIS 6.0 on Windows Server 2003 has no trouble doing what you're looking for.

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Windows Server 2003 runs IIS 6.0, not 5.1. – Massimo Nov 30 '11 at 21:16
@Massimo: Brain fart... good catch! – Evan Anderson Nov 30 '11 at 21:18

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