On 16 February 1944, the day after the contentious destruction of Monte Cassino, Eaton took No. 3 Squadron through a break in the bad weather to attack the ruined monastery, the only one of No. 239 Wing's units to successfully bomb its target that day. He handed over command of No. 3 Squadron later that month, and was transferred to No. 1 Mobile Operations Room Unit as forward air controller for the final assault on Monte Cassino. The run of luck that Eaton experienced in his first weeks of air combat in Tunisia continued on the ground in Italy. He survived three months of constant artillery fire, including an occasion when a shell exploded directly above his observation post, striking down a British officer standing next to him. He also came under machine-gun fire when he took a wrong turn one day and drove into the German lines, but again escaped unhurt. He was awarded the Distinguished Service Order on 7 April, in recognition of his leadership of No. 3 Squadron in North Africa, Malta, Sicily and Italy.