I'm not sure if I am following you completely, so follow up if I am missing something. It sounds like John Doe/OU/Org will appear in the query, but Jane Doe/Org does not? If this is the case, then I would think that your search base is set to filter to the OU level, where OU1 in the Directory Assistance database is not set to "*", and perhaps the ORG is also not set to "*".
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