The Abbey of Monte Cassino overlooked the only north-south road from Naples to Rome. The promontory, studied by the Italian War College as an example of a position made impregnable by nature, was the focal point of the German Gustav Line. The Fifth Army was obligated to conduct a winter campaign to break through the Gustav Line and relieve the troops at the Anzio beachhead. On 15 February 1944, 253 tons of explosives were dropped on the Abbey of Monte Cassino. The author reviews the reasoning for the bombing why it was deemed necessary.