Custom Watermarked Textbox behaving strangely

Answer 1

You're just missing a Refresh at the end of the DisableWaterMark sub:

Private Sub DisableWaterMark()
    Me.waterMarkTextEnabled = False
    Me.SetStyle(ControlStyles.UserPaint, False)
    If oldFont IsNot Nothing Then
        Me.Font = New System.Drawing.Font(oldFont.FontFamily, oldFont.Size, oldFont.Style, oldFont.Unit)
    End If
    Refresh()
End Sub

EDIT:

Rather than using the UserPaint control style, you can handle the WM_PAINT message in WndProc, and only print the watermark if the text is empty. The result is basically the same though.

Protected Overrides Sub WndProc(ByRef m As System.Windows.Forms.Message)
    MyBase.WndProc(m)
    Const WM_PAINT As Integer = &HF
    If m.Msg = WM_PAINT Then
        If Text.Length <> 0 Then
            Return
        End If
        Using g As Graphics = Me.CreateGraphics
            g.DrawString("Water Mark", Me.Font, Brushes.LightGray, 0, 0)
        End Using
    End If
End Sub

Protected Overrides Sub OnTextChanged(ByVal e As System.EventArgs)
    MyBase.OnTextChanged(e)
    Invalidate()
End Sub

Protected Overrides Sub OnLostFocus(ByVal e As System.EventArgs)
    MyBase.OnLostFocus(e)
    Invalidate()
End Sub

Protected Overrides Sub OnFontChanged(ByVal e As System.EventArgs)
    MyBase.OnFontChanged(e)
    Invalidate()
End Sub

Answer 2

there is something here and here that could maybe help you