[bobbenedetti]

You may want to check how your IT dept has Outlook Anywhere configured. When I set up the email account for my Exchange Server the certificates download on the first connect and are saved. The message is something like the server has to do a security setup on the phone. But it happens only then. Every other connect results in an immediate download of mail (if I do a manual Sync which I rarely do because I am using Microsoft Push email).
Exchange certificaates can be really tricky if they are not set up exactly right.