I recently had to re-install SBS2008 at a client site. I can't remember how I setup the self-signed certificate authority on the server in order for Outlook to correctly work without the attached screen shot pop-up. I have tried 6 ways from sunday to install the certificate. E-mail works, OWA works, I just need this pop up to go away. I'm hoping someone more versed in Certificate Authority and exchange could help.