Wynn made his first combat jump into Normandy on D-Day. He linked up with other members of E Company. He participated in the Brécourt Manor Assault. When the group was attacking the first gun, Wynn was shot in the buttocks and fell into the trench. Wynn apologized to Winters, who was leading the attack, "I'm sorry, Lieutenant, I goofed. I goofed. I'm sorry." Later Winters in his biography "Beyond the Band of Brothers" wrote, "My God, it's beautiful when you think of a guy who was so dedicated to his company that he apologized for getting hit. Now here was a soldier – hit by enemy fire in Normandy on D-Day, behind the German lines, and he is more upset that he had let his buddies down than he was concerned with his own injury. Popeye's actions spoke for all of us". Carwood Lipton and Mike Ranney found Wynn on his way back to safe area, and they helped to apply sulfa on his wound. Wynn was then evacuated to Utah Beach, and was sent to a field hospital in England. Wynn was awarded the Bronze Star Medal and the Purple Heart for his action.