Setup IIS 7.5 with multiple website bindings and SSL?

Solution 1:

Without SNI extensions, you can bind only one SSL certificate per IP:port pair. If you need to run 2 HTTPS on the same IP -- bind them to different ports and then refer to such site providing port in URL (e.g. https://beta.example.com:444/). You can use the same wildcard certificate on different ports without any issue.

If you have more than one site with blank host name (for HTTP protocol), then the one with lower ID should be a "catch all". The same goes for HTTPS -- the one with lower ID should intercept all requests on that port.

On another hand, you have a wildcard certificate and I have seen one article which tells that this can be done in IIS7: http://www.sslshopper.com/article-ssl-host-headers-in-iis-7.html . I tried it myself in the past, but it did not worked well for me -- quite often IIS was throwing a 5xx error when accessing even static files (which stopped happening when we bind another host to a different port). Maybe it has been fixed since then.

Solution 2:

Server Name Indication is not yet supported in IIS 7 or 7.5. Hopefully they will implemented this feature in the next IIS: http://forums.iis.net/p/1161905/1923273.aspx

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Solution 3:

Although this is an older question, I had a need to accomplish the same thing just recently. It can be done under IIS 7.x by use of Subject Alternate Name certificates. These certificates are preferable to wildcards because it will restrict itself to only the sites specifically listed, thus mitigating attacks based on spoofing a bogus site name within a domain captured under a wildcard.

Once the SAN certificate is imported into IIS, you can use the appcmd tool to specify the additional binding or manually edit applicationHost.config within the section, eg

<site name="SomeSite" id=9>
   <bindings>
     <binding protocol="http" bindingInformation="*:80:SomeSite"/>
     <binding protocol="https" bindingInformatoin="*:443:SomeSite" />
   </bindings>
</site>