Ssl – Multiple ssl certificates with one ip and same port but different host headers (IIS 8)

You can't assign different SSL certificates to sites that are only differentiated by host headers. You would need to have the sites on separate IP addresses.

Another option is to setup a wildcard SSL certificate (which you could then apply to all sites hosted under *.example.org on the server.) There is a catch though - you still can't apply the certificate through the GUI. Instead you need to use a command line to apply the certificate.

http://www.sslshopper.com/article-ssl-host-headers-in-iis-7.html http://blogs.iis.net/thomad/archive/2008/01/25/ssl-certificates-on-sites-with-host-headers.aspx

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.