How can I publish on ISA multiple SSL sites using the same IP address and port, with different certificates?
You can only use one SSL certificate per listener. If all sites are published using the same domain name, you can use a wildcard certificate, and then use a single IP address and a single listener to publish multiple sites. For example, if you are trying to publish the following sites: OWA, WebSite1, WebSite2 at domain.com, you can acquire a wildcard certificate for the ISA Server computer for *.domain.com. It’s also possible to add different domain names in addition to wildcards depending on the achieved validation level. For more information about wildcard certificates see also question #38.