Thank you for this. Select Case worked for me however, I got an error with FillBM; not sure if I was supposed to substitute something there. I used the following and it works.

Select Case True
Case Chbx2 = True And Chbx3 = True And Chbx4 = True And Chbx5 = True And Chbx6 = True
Selection.TypeText Text:= "First", "CheckBox2, CheckBox3, CheckBox4, CheckBox5 and CheckBox6"
Case Chbx2 = True And Chbx3 = False And Chbx4 = True And Chbx5 = False And Chbx6 = True
Selection.TypeText Text:= "First", " CheckBox2, CheckBox4 and CheckBox6"
End Select


Content Controls, I am not familiar with but I am going to try it.