Recently I ran into a problem with one our customer. They have a quite unique namespace deployment for Exchange 2010. The OWA is published through URL
https://webmail.companyA.ITcompany.com/owa
https://webmail.companyA.ITcompany.com/owa. But the primary email address is username@companyA.com. I bought a SSL cert with following SANs
- webmail.companyA.ITcompany.com
- autodiscover.companyA.ITcompany.com
- InternalExServerName
- InternalExServerName.companyA.local
The problem comes when users access Exchange from a non-domain joined client with either Outlook2007 or 2010. They will receive cert error as by default it lookup to autodiscover.companyA.com
Customers can live with this issue as long as they click Yes to confirm the certificate error. I have not tried Outlook Anywhere though, will Outlook Anywhere use autodiscover.companyA.ITcompany.com or autodiscover.companyA.com? and how about ActiveSync...?