The serene hilltop abbey of Montecassino has unfortunately been the center stage for a number of conflicts and destructions throughout history, most recently in World War II. In the winter of 1944 thousands of Allied bombs were dropped on Montecassino, completely reducing the historical and holy site to ruins and taking the lives of many. Though it isn't unusual for important sites and civilian cities to be destroyed during the course of war, the decision to bomb Montecassino was not an easy one to make, and still remains a controversial subject for some.

During this stage of World War II, frustrations were high and the battles grew increasingly more violent. Following the Armistice of Cassibile between Italy and the Allies in September of 1943, Italians found themselves in an awkward and dangerous position. Although Italy had signed a peace treaty, it was still at the epicenter of the war as German forces remained and continued to fight back against the Allies. The town of Cassino, located down the hill from the abbey, was bombed heavily months before the bombing of Montecassino, killing thousands of civilians and leaving many others to find somewhere safe to take refuge. Some civilians fled to Montecassino, in the hopes that it would be untouched during the war. Many of the refugees who remained during this time also helped in the effort to evacuate many of the artifacts, library archives and documents, and numerous other priceless treasures from the monastery to Rome shortly before the bombardment. Cassino was eventually completely destroyed in March of 1944. Photos of the final bombardment can be seen in Montecassino's museum.

Montecassino was at a strategic point for the Allied forces to breakthrough German defenses in order to take Rome and hopefully end the war. Allied intelligence differed in regards to the exact occupants of the abbey. Some believed it was being occupied as an outlook and artillery post by German troops, while other official statements (including some by the abbot Gregorio Diamare himself) insisted that it was only harboring Italian refugees and monks and no German troops. Others still reasoned that even if there were no enemy forces already occupying the abbey, it was inevitable that they eventually would due to its location, which would jeopardize the Allies push up the Valley towards Rome.

The Allies went through with the deadly bombardment on February 15th of 1944. Abbot Diamare and the remaining monks fled to Rome for safety after. No German troops were among the dead from the bombing but instead many Italian civilians were. German forces immediately utilized the rubble for cover to try and prevent the Allies from pushing onward to Rome. The monastery was finally captured on May 18th by Polish soldiers, after many months of violent conflict and an immense loss of life. Allied forces captured Rome soon after, on June 4th .