I have been in the process of learning and setting up a hybrid solution for our current Exchange environment in order to migrate to Office 365. I was attempting to go the route of obtaining an SSL for our AD server in order to sync SSO with Microsofts AD FS as I understand it. The problem arose when our internal fqdn is the name of an outside DNS. Whoever set it up used contoso.com for internal and emaildomain.net for our Exchange domain. So I can not attempt this method. My question is, can I simply duplicate our current wildcard emaildomain.net cert and create hybrid environment in that way? Are there alternate simpler methods of creating the hybrid environment?