I just found this KB at Blackberry.com for Desktop Manager 4.3. This explains why Outlook doesn't show up as a program to sync with. Keep those versions of DM 4.2 around if you use Outlook 2000 (as I do.)

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Unable to select Microsoft Outlook 2000 from the list of programs for synchronization

Doc ID : KB14763
Last Modified : 2007-12-13
Document Type : What Is


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Environment

• BlackBerry® Desktop Manager 4.3
• Microsoft® Outlook® 2000

Details

BlackBerry smartphone users who have Microsoft Outlook 2000 installed on their computers are unable to select Microsoft Outlook from the list of programs for synchronization. Support for Microsoft Outlook 2000 has been removed in BlackBerry Desktop Manager 4.3.




Additional Information

A list of alternate programs for synchronization can be found at http://na.blackberry.com/eng/services/desktop/req_4dot3.jsp


Products & Services:

• BlackBerry Desktop Software