Hello,
I've noticed this issue for our Outlook 2010 users (all are outlook 2010 running on Exchange 2010 DAG) they the 'autodiscover.domainname.com pops up 'each time' starting an Outlook Anywhere session from outside the office. Once clicked 'Yes' to this pop up the Outlook gets connected.
I tried to install this certificate to Trusted Root Certificates folder but again, after closing and re-opening the Outlook it again appears once.
Any fixes?