Recently we attempted to move from a wildcard certificate on our Exchange 2010 single server to a digicert SSL certificate. The process seemed easy enough but we found that Autodiscover Outlook clients were getting: "There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name of the target site usmail.company.com" and would prompt for credentials. It would never resolve the credentials and continue to prompt, thus never connecting Outlook.
We ensured the cert SANS included autodiscover.company.com as well as all the other to include POP, and IMAP.
What are we missing the server worked fine with the wildcard cert?
Thank you in advance.