The following will do what you ask:
Code:
Private Sub Document_ContentControlOnExit(ByVal ContentControl As ContentControl, Cancel As Boolean)
Dim strDetails As String
Dim oCC As ContentControl
Dim oRng As Range
Set oCC = ActiveDocument.SelectContentControlsByTitle("Grade").Item(1)
Select Case oCC.Range.Text
Case "LOW"
strDetails = "7.1.5 Umbrella Insurance with a minimum limit of not less than $2,000,000 per" & vbCr & _
" occurrence."
Case "MINIMAL"
strDetails = " "
End Select
If ActiveDocument.Bookmarks.Exists("BM7") Then
Set oRng = ActiveDocument.Bookmarks("BM7").Range
oRng.Text = strDetails
oRng.Bookmarks.Add "BM7"
Set oRng = ActiveDocument.Bookmarks("BM7").Range
With oRng.Find
Do While .Execute("Umbrella Insurance")
oRng.Font.Underline = wdUnderlineSingle
Exit Do
Loop
End With
Set oRng = ActiveDocument.Bookmarks("BM7").Range
With oRng.Find
Do While .Execute("2,000,000")
oRng.Font.Bold = True
Exit Do
Loop
End With
Set oRng = ActiveDocument.Bookmarks("BM7").Range
With oRng.Find
Do While .Execute("7.1.5")
oRng.Font.Bold = True
Exit Do
Loop
End With
End If
lbl_Exit:
Exit Sub
End Sub