Outlook 2007 clients connecting to internal Exchange server( are prompted to accept certificate with message "The name on the security certificate is invalid or does not match the name of the site." The name on the certificate is that of our external URL for OWA. The host name in use for the external url resolves to our public IP address and the host name internally resolves to the internal ip address of the server running Exchange 2007.
Once accepted Outlook works fine until the next restart when prompted again for the certificate. We recently installed Exchange 2007 SP2 because of Outlook prompting for authentication, which helped but this prompt remains.
Additionally I can use hosts file entry pointing the external url to the internal ip address for exchange which resolves the prompting, however breaks out of office assistant.
Any assistance is greatly appreciated. Thank you.