It could be that the error is on the PC side and not the BB. The BB is trying to interact with a windows program (Outlook) via a windows program (DM) and is not allowed to do so for some reason. But I have also seen where it might be a BB issue.
What version of Outlook are you using?
Try turning Dr Watson off and see if it works as it should. How to disable or enable Dr. Watson for Windows
Another place to check would be the RIM knowledgebase.
If this doesn't help, please post the exact error message if possible.