How to get the Microsoft CRM 2011 Outlook Plugin to authenticate

One thing that could be worth checking is if the Exchange Address Book service is running, as it tends to start a bit early with the latest patches for Exchange, and then fail starting up.

My coworkers and I are having the same problem when replying to encrypted emails. For emails originating from within our domain and published in the global address list, we can reply encrypted just fine. However, for associates outside our network who we've done manual key exchanges with, hitting reply or reply all results in Outlook unable to resolve their certificate from the local contact list. Prior to hitting send, the emails are treated as one entity in that clicking on one and hitting delete will remove it, but once "send" is pressed, the certificate look-up fails instantly and their address becomes an unassociated group of letters which have to be deleted like test. Curiously, when send is pressed, we get the error message twice and have to hit "cancel" both times. Once we delete the addressees, then re-add them manually, outlook resolves their certificates and happily sends the email.

What I have noticed is this behavior is associated with the mail profile. My laptop was happily replying to all encrypted emails until I corrupted my profile and had to create a new one. From that point on I was no longer able to reply to encrypted emails from outside our company unless I delete then re-type the addressees one at a time.

In summary, the issue appears to be Outlook's inability to associate incoming email addresses with local contacts for the purpose of certificate retrieval. I suspect when it occurs, this happens for all non-GAL emails, but it only really becomes apparent when encrypting.