Problem
BlackBerry Desktop Software 4.2
Microsoft Outlook

While synchronizing the Address Book using Synchronize in BlackBerry Desktop Manager 4.2, the following error appears:
Desktop Manager has encountered a problem and needs to close.

Cause
One or more Contacts in Microsoft Outlook has an associated picture.

Resolution
Remove the pictures from the Contacts in Outlook.

OR

If you do not know which Contacts have associated pictures, enable advanced logging for the Synchronize application. For instructions see Blackberry link here