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How do I host multiple SSL websites(all subdomains) using ISA inbound rules with 1 external IP address?

I think something like option 2 in this question might work?

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up vote 1 down vote accepted

In addition to using a wildcard or SAN cert, you will need to set up SSL Host Headers on IIS: http://www.sslshopper.com/article-ssl-host-headers-in-iis-7.html

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At the minimum you will need a server certificate which supports wildcards (if both of the hostnames are under the same DNS domain) or a certificate with more than one name (if not.)

Once you have that, the remaining should be pretty easy.

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+1, you need 1 IP per Cert; so the Cert has to cover all the possible domains people will connect to. –  Chris S Apr 30 '10 at 1:37
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