Herrington served as both a turret gunner and radio operator on a B-24 Liberator. It was on August 3, 1944, that Herrington's plane would take off from Pantanella Air Base, Italy, at 1137. Skies were clear with some scattered clouds. The bombing mission of Friedrichshafen was complete and they were on their way back. Enemy fighter planes stormed in and attacked the bomber formation. Many planes were damaged and a lot of parachutes were seen descending from the sky. Herrington's bomber went down in flames, he was not able to escape before it hit the ground in Lermoos, Reutte Bezirk, Tyrol (Tirol), Austria. Four crew mates of his managed to jump out of the plane. The pilot, 1st Lieutenant Fiecoat was one of them. When he landed, he was executed by civilians Austria. The other three crew members were captured and kept as prisoners of war. This was Herrington's 40th and final mission