On 7 April 1940 Cheshire was promoted to flying officer and in June he was posted to 102 Squadron, flying the Armstrong Whitworth Whitley. 102 Squadron was in 4 Group of Bomber Command, and shared the airfield at RAF Driffield with 77 Squadron. Cheshire remarked that upon arriving at Driffield he was filled with a fear that he would not measure up to what was expected of him, but soon found himself buoyed with the sense of being part of a tradition. He became good friends with a number of pilots there, including Hugh "Lofty" Long and Jimmy Marks.