Communicator Error ID:5001 "The following message was not delivered"

I have recently encountered this error in an OCS 2007 deployment with a mix of Communicator 2007 and Communicator 2005 clients. The problem was specifically that the Communicator 2005 client did not have the latest hotfix installed: http://support.microsoft.com/kb/949280/ (released December 19, 2008). The Communicator 2007 client had the latest hotfix, but not the Communicator 2005 client.

Another possibility for this error when it involves two internal IM clients and an OCS 2007 server, is an OCS 2007 server issue with the IM filter application not being able to read from WMI. The presence of a specific event in the server event log will confirm that this is the problem. The event-id specifics and resolution is documented in Microsoft Knowledge Base article 943392: http://support.microsoft.com/kb/943392

If an internal user is getting this error while attempting to communicate to an Public IM recipient, it is likely a problem with your Edge server, the Edge PIC configuration, the remote PIC gateway, or the format of the IM address being used to try and reach the recipient. The following links document the most common problems:

Changes to Yahoo! IM federation may affect users of Office Communications Server 2007 and Live Communications Server 2005

IM fails to send to Corporate AIM

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