As a first lieutenant, Winters parachuted into Normandy in the early hours of D-Day, June 6, 1944, and later . After the German surrender in May 1945, he left the 506th and was stationed in France, where senior officers were needed to oversee the return home. In 1951, during the Korean War, Winters was recalled to the Army from the inactive list and briefly served as a regimental planning and training officer on staff at Fort Dix, New Jersey. After volunteering and completing training to become a Ranger, Winters was issued orders for deployment and was preparing to depart for Korea, but instead left the Army under a provision that allowed officers who had served in World War II but had been inactive since to resign their commission.