Winters arrived at Toccoa in mid-August 1942 and was assigned to Company E, 2nd Battalion, 506th PIR, which later became better known as "Easy Company" in accordance with the contemporaneous Joint Army/Navy Phonetic Alphabet. Serving under First Lieutenant Herbert Sobel, Winters was made platoon leader of 2nd Platoon, earning a promotion to first lieutenant in October 1942 and made acting company executive officer, although this was not made official until May 1943. The 506th PIR was an experimental unit, the first regiment to undertake airborne training as a formed unit. The training at Toccoa was very tough. Of the 500 officers who had volunteered, only 148 completed the course; of 5,000 enlisted volunteers, only 1,800 were ultimately selected for duty as paratroopers.
