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I have a single IIS 6 box (Win2k3 SP2) that I host multiple development websites on. I have one site currently that requires SSL and now I'm adding a second site. The first site is bound to the machine's IP of and is working just fine. I've added the second site, added to the list of valid IPs for the machine and bound the second site to that IP but now I'm stuck.

We only have a single public IP and our router (running DD-WRT v24-sp1) is redirecting all incoming requests to ports 80/443 to the first IP address so I have no way of getting people to the second site over SSL now.

So I guess I just need confirmation that I'm going to have to do something different. Getting a second IP from our ISP isn't an option (they want too much and take too long to get anything done). Is a wildcard cert the route to go down? Can I create one with openssl? ( I don't mind the browser warning.)

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up vote 1 down vote accepted

You should be able to host both sites on one server. Just add a second site to IIS, assign the site name and SSL certificate to it, and assign both A records to the same IP. You'll only be able to browse to it by hostname, but SSL requires a valid hostname anyway.

Edit: You're gonna have to get a wildcard for this, though. They're relatively cheap at least. If you're self-signing with OpenSSL, here's how to create a wilcard SSL cert:

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you have to share the docroot for this to be even possible so the sites need to have a common code – anthonysomerset Mar 18 '11 at 20:19
Are you sure you're not thinking Apache? – Hyppy Mar 18 '11 at 20:23
Thanks @Hyppy, that worked! I used the OpenSSL instructions from here and IIS instructions here… – Chris Haas Mar 18 '11 at 21:00

You could change the port of the second SSL site or you need to use TLS, but other than that you need a second IP.

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Thanks, I forgot to say that I didn't want to introduce an alternate port. – Chris Haas Mar 18 '11 at 20:06
Well, then your looking at my last to options then. – Jacob Mar 18 '11 at 20:10
Thanks for trying @Jacob! – Chris Haas Mar 18 '11 at 20:29
Sorry Typo, I meant that you could use TLS or get another IP... Thats about it – Jacob Mar 18 '11 at 20:35
Thanks @Jacob, I went the wildcard route and its working just fine now – Chris Haas Mar 18 '11 at 21:01

to use a single IP you need to use a wildcard SSL, however to do this you would need to use a reverse proxy which can act as an ssl endpoint which can then send requests for one domain back to its ssl site and the other to its website

to be able to do proper ssl you still need 2 ip addresses as there aren't any servers to my knowledge that can do name based ssl vhosts because the name headers are negotiated after ssl negotiation

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