I have a single IIS 7 server with a single IP address. Site 1 has an SSL cert for www and Site 2 has a wildcard SSL cert for various subdomains. Both sites use host headers to d
Until SNI is fully supported, you can only have one certificate per IP address. If you can get a certificate that covers both sites (a wildcard or a UC certificate, for example), you can set up SSL Host Headers to allow both sites to be secured.