What error do you receive on the external certificate? You can only bind a single certificate to a service on a IP, so you would need to put ISA or another CAS box in front.... most people are now using certificates with multiple Subject Alternative Names (SANs) however. This way you need one certificate with all of the names.
- Joel
Doug and I spoke on the phone and this is how we got to the bottom of his problem.
To walk through the process
Some of the common errors for AutoConfiguration:
0x80072EE7 – ERROR_INTERNET_NAME_NOT_RESOLVED
This error is usually caused by a missing host record for the Autodiscover service in the Domain Naming service.
0X80072F17 – ERROR_INTERNET_SEC_CERT_ERRORS
This error is usually caused by an incorrect certificate configuration on the Exchange 2007 computer that has the Client Access server role installed.
0X80072EFD – ERROR_INTERNET_CANNOT_CONNECT
This error is usually caused by issues that are related to Domain Naming service.
0X800C820A – E_AC_NO_SUPPORTED_SCHEMES
This error is usually caused by incorrect security settings in Outlook 2007.