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At what point during a migration from Exchange 5.5 to Exchange 2003 does the Outlook client start to use Active Directory for its name resolution?
By name resolution, you are asking about resolution of SMTP e-mail addresses (rather than DNS name resolution). Exchange 5.5 has its own directory so Outlook checks there when resolving an SMTP address on the To: or Cc: lines. Once your mailbox has moved over to Exchange 2003, the SMTP address goes to the Active Directory for resolution.