Simply put, the compressor should turn off when the pressure reaches the cut-out point and restart when the pressure decreases to the cut-in point. The cut-in pressure, hence, is never higher than the cut-out one.
It is the best practice that you set the pressure difference between these two points at least 14 PSI. Otherwise, the compressor might start and stop repeatedly over a short time. Also, you must always set the cut-in point first, the cut-out point goes second.