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Reporter
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| VBOffice Reporter is an easy to use tool for data analysis and reporting in Outlook. A single click, for instance, allows you to see the number of hours planned for meetings the next month. | 
This macro is less about the receiver getting your message with an assigned category but more about you quickly finding the sent message in your own folder by using keywords. The script prompts you if a category is missing. You can then cancel the sending.
Private Sub Application_ItemSend(ByVal Item As Object, Cancel As Boolean)
  On Error Resume Next
  Dim Msg$
  If Len(Item.Categories) = 0 Then
    Msg = "Do you want to add a category?"
    If MsgBox(Msg, vbYesNo Or vbQuestion) = vbYes Then
      Cancel = True
    End If
  End If
End Sub