Cheshire was posted to 35 Squadron in January 1941, where he joined Jimmy Marks, "Willie" Tait and George Holden. The squadron was converting to the new four-engine heavy bomber, the Handley Page Halifax. His time in 35 Squadron included seven raids on Berlin. Cheshire was promoted to acting squadron leader on 1 March 1941, and was awarded the Distinguished Flying Cross (DFC) later that same month. Losses among Bomber Command continued. Four months after Cheshire completed his DSO mission, "Lofty" Long was killed during a mission on 13 March 1941. It was another close personal loss for Cheshire. "Whatever outward face I may have put on it, his loss affected me very deeply, and the memory of what I owed him and of all that he stood for remained with me throughout the war."