So you want to play with SSL certificates on Windows 2008 (R2)?
Well the you probably already know that SSL & Host Headers don’t mix in IIS 7 (well not via it’s GUI anyway!)!
But never fear, even though the GUI is pathetically incapable of working with host headers & SSL, you can achieve what you want via the command line;
1. Within IIS bind the certificate to all the sites you want to use it on (Host Header will be greyed out… hmph…).
2. Fire up good old “cmd” & go to “C:\Windows\System32\Inetsrv\” .
5. Run the following command for each website on the IP address that you want to use the certificate for (copy both lines):
appcmd set site /site.name:”<WebSiteName>” /+bindings.[protocol=’https’,bindingInformation=’*:443:<HostHeaderValue>’]
Replace <WebSiteName> with the name of the IIS site and <HostHeaderValue> with the host header for that site.
See, simple! There’s always a way! 😉