IIS SSL Certificate issue

If multiple SSL Certificates are used, the server usually has a problem with providing the correct SSL Certificate when an HTTPS connection is established, causing a certificate name error.

You are going to need to get a new certificate that can cover more than one website (wildcard or UC certificates).

A wildcard certificate secures any subdomain of the domain that it was issued to. For example, a certificate that is issued to *.domain.com will cover something.domain.com, anything.domain.com, and whatever.domain.com. Because the *.domain.com certificate is valid on any of these domains, you will not receive an error message.

Also good to note: you can't use the IIS7 User Interface to add a host header to an SSL site binding. You have to use command-line tools, do it programmatically or edit applicationhost.config directly. Here is an example and a link how you can it via command-line:

appcmd set site /site.name:"MySite V2" /+bindings.[protocol='https',bindingInformation='*:443:sitev2.mysite.com']

And last but not least: with IIS7 you can use the following command to figure out what certificate is bound to a particular IP:Port combination:  
netsh http show sslcert

This command will show the IP:Port binding but also some other SSL settings.

The above applies even with multiple IP's on the server?