During World War II, he was assigned to the 3rd Battalion, 24th Marines, 4th Marine Division. Captain Sawyer took part in the battles of Kwajalein, Saipan, and Tinian as the battalion operations officer. At Saipan, he also assumed the role of executive officer of the battalion when the original executive officer was wounded. He was awarded a Bronze Star for his actions at Saipan. Webb was promoted to major, where he assumed the position of regimental operations officer for the 24th Marine Regiment during the battle of Iwo Jima.