This way UserForm1 never closes if CommandButton2 is clicked.
And in case of the MsgBox, Userform1 closes after the MsgBox is dismissed.
In other words, MsgBox keeps the timer from firing until it is dismissed.

Thanks.

Emile

Perhaps:

Regular Code Module:

Public dFireTIme As Double


UserForm1:

Private Sub UserForm_Activate()
dFireTime = Now + TimeSerial(0, 0, 5)
Application.OnTime dFireTime, "closeThisForm"
End Sub

Private Sub CommandButton2_Click()
Application.OnTime dFireTime, "closeThisForm", Schedule:=False
UserForm2.Show
End Sub

UserForm2:

Private Sub UserForm_Deactivate()
Application.OnTime Now + TimeSerial(0, 0, 1), "closeThisForm"
End Sub