Greetings. I have little experience with SSL certificates so please bear with me.
I have read and found that normally multiple SSL enabled sites cannot be run in IIS with a single IP address. Here is what I tried and I would like anyone to tell me what will happen if I continue with this setup.
I have my original SSL enabled site up and running just fine on Windows Server 2003/IIS using port 80 for TCP and port 443 for SSL and a valid active SSL certificate installed. On the same instance of IIS I have another site that I have set up to use port 80 for TCP and port 444 for SSL using a self generated development SSL certificate. I have found that browsing to the second site using https://www.domain.com/ it brings up the original site with a warning that the SSL certificate does not match the URL in the certificate. That's fine, no problem there. If I browse to https://www.domain.com:444/ it brings up the second site with the usual development certificate warnings. I haven't rigorously tested the site but it appears to be working well.
What I want to know is if I am going to run into any problems on this server if I continue operating this way.