SSL Host Headers? Does it really exist?

Yes however somewhat tricky.

  • You need to have a Wildcard or *.domain.com SSL certificate.
  • Your domains need to be all sub-domains of the wild card domain
  • You just can’t do it using the IIS inetmgr user interface.

http://technet2.microsoft.com/WindowsServer/en/library/1032c063-e372-4875-9a31-d6de8e1e87921033.mspx?mfr=true

In short, to add an SSL host header, run the following:
cscript.exe adsutil.vbs SET /w3svc/<site identifier>/SecureBindings “:443:<host header>“

To get the site identifier you can run the following:
cscript.exe adsutil.vbs ENUM Path “/P”