Our current cert is about to expire and we are looking at putting in a SAN cert to help ease some issues we are having with Outlook anywhere and autodiscover. I am the messaging administrator for a State's email system and we are responsible for 130 state agencies email. So according to my calculations I would need to have 260 plus names in a SAN cert to accommodate both autodiscover and the email domain, which I have been told by our certificate vendor would not work because it would be too large and we need to break it up into smaller chunks of 20 names per SAN cert. I would like to use a wild card cert, but this is an issue since the email addresses we are authoritative for do not all end in the same suffix (most email domains are state.gov, but we have a few that end in .org). So my question is, can you add multiple SAN certs to the CAS servers? As far as I can tell you can only enable one cert to a service. I have not found any documentation about this and just wondering if anyone had any suggestions.

Take a look at this article: Understanding Redirection for Outlook Anywhere with a Single SSL Certificate Perhaps you might also offload SSL to an appliance or TMG where different certificates would be configured for different URLs? Mike Crowley | MVP My Blog -- Planet Technologies

Thanks for getting back with me. I will take a look at both of these options to see what will work best for our organization.