Private Sub Document_ContentControlOnExit(ByVal ContentControl As ContentControl, Cancel As Boolean)
Dim lngIndex As Long
  Select Case ContentControl.Title
    Case "Test"
      For lngIndex = ContentControl.DropdownListEntries.Count To 2 Step -1
         ContentControl.DropdownListEntries(lngIndex).Delete
      Next
      Select Case ContentControl.Range.Text
        Case "A"
           ContentControl.DropdownListEntries.Add "A.I", "A.I"
           ContentControl.DropdownListEntries.Add "A.II", "A.II"
           ContentControl.DropdownListEntries.Add "A.III", "A.III"
        Case "A.I"
           ContentControl.DropdownListEntries.Add "A.I.a", "A.I.a"
           ContentControl.DropdownListEntries.Add "A.I.b", "A.I.b"
           ContentControl.DropdownListEntries.Add "A.I.c", "A.I.c"
        Case "B"
           ContentControl.DropdownListEntries.Add "B.I", "B.I"
           ContentControl.DropdownListEntries.Add "B.II", "B.II"
           ContentControl.DropdownListEntries.Add "B.III", "B.III"
        Case "C"
           ContentControl.DropdownListEntries.Add "C.I", "C.I"
           ContentControl.DropdownListEntries.Add "C.II", "C.II"
           ContentControl.DropdownListEntries.Add "C.III", "C.III"
      End Select
  End Select
End Sub