Exchange 2010 Outlook Anywhere cert error but only after successful login
Posted on 2012-03-13
I have a new Exchange 2010 installation. I've purchased a UC/SAN certificate with a number of alternative names included to cover the FQDN of all CAS/HT servers as well as autodiscover and the standard recommended name.
I've installed the cert on our hardware loadbalancer and set up SSL offloading.
When I connect using Outlook 2010 and Outlook Anywhere, the autodiscover service works fast and perfectly sets up the account and then I can connect Outlook without incident.
However, 30-45 seconds after a successful login and without interrupting anything I get a security alert. It appears to reference the self-signed cert created in the installation of Exchange. I'm not sure what is triggering the need for the cert. The top of the error shows the FQDN of one of my cas/ht servers which is included in my UC/SAN cert.
I'm pretty sure this something that is not being properly pointed to by my load balancer but I'm not sure what it is. I currently have ports 110, 143, 993,, 25, 587, 443 and 80 setup for load balancing.
What am I missing? Any help appreciated.