We have an Exchange 2010 server. We have a public SAN SSL Certificate covering mail.domain.com, exchange.domain.com, autodiscover.domain.com. We have 1 internal AD domain - domain.com. The Exchange server is called Exchange, so the Certificate covers internal and external usage. No problems using it for ActiveSync or OWA. The problem is Outlook Anywhere. We have a dozen email domains. So if a user's email address is firstname.lastname@example.org, when running Outlook Anywhere they use the SAN SSL Certificate, but get a warning because autodiscover.domain2.com is not listed in the Certificate. I do not want to buy certificates for every email domain. Is there anyway around this? When we setup Outlook Anywhere, the server name is Exchange and the proxy server is exchange.domain.com. No where is the setup do we put anything about domain2.com, other than its the user's email address.