| For diagnostic purposes, Outlook contains an option that turns on the logging of certain Outlook features. |
Enable Outlook 2007 / 2010 Client Logging
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A self-signed Microsoft Exchange 2007 Security Certificate is valid for a period of one year. After this period you’re required to re-issue a new certificate. This can be done using EMS (Exchange Management Shell) and the New-ExchangeCertificate CommandLet (cmdlet).
If you do not update / reissue the certificate, Outlook will complain about this issue displaying a Security Warning on the users display (this one’s in German).

Outlook_SecurityWarning Certificate not valid
Step-by-step (quick tutorial):