He was the jumpmaster on one of the C-47 Skytrains during the American airborne landings in Normandy in the early-morning hours of 6 June 1944. Parachuting into the Cotentin Peninsula, he was able to rendezvous with First Lieutenant Richard Winters and several others from the 101st- and 82nd Airborne Division. They were later reunited with several more Easy Company members and worked their way just south of their objective of Carentan. During the Battle of Normandy, Lipton was lightly wounded by German 88 mm shrapnel.