The Short Stirling was the first of the RAF's famous trio of four-engine heavy bombers used during the night offensive over Europe. The Stirling was the produced of a highly ambitious pre-war requirement for a heavy bomber capable of carrying an unprecedentedly large bomb load over long distances. The result was an aircraft that exceeded its two successors in size. Despite its towering shape, the Stirling proved to be highly maneuverable in flight thanks to its thick wings although in terms of performance it suffered compared to other heavy bombers due to its more limited range and maximum service ceiling. Problems arose because of its short shoulder-mounted wings which required a huge landing gear. This gave the aircraft an impression of massive size when on the ground though it proved beneficial for shorter take-offs. Its shallow bomb bay, divided into three compartments, also limited the size of individual bombs which it could carry (500-lbs maximum). Furthermore, payload had to be considerably reduced for longer range missions which also put it at a disadvantage with the Halifax and Lancaster which could carry heavier loads at longer distances. Stirlings were first employed in early 1941 (initially for daylight operations) and were used in some of the early raids against Berlin as well as the first 1,000 bomber raids. They were also the first to carry Oboe radar and fly Pathfinder missions. By 1943, most Stirlings had been retired from service as its more advanced successors became available although later variants were developed as tugs and transports until replaced by the York in 1946.

The first prototype S.29 flew in 14 May 1939 but was destroyed in flight. Initial production variant was the Mk. I with Hercules XI radials while the Canadian-built Mk. II with Wright Cyclone engines only reached the prototype stage and none were used in combat. The principal variant eventually became the Mk. III with Hercules XVI engines and a dorsal turret, which was first installed in some late Mk. Is. This variant also included numerous Mk. Is which were converted to Mk. III standard. Final variants included the Mk. IV transport and glider tug and the Mk. V transport which could carry up to 40 troops or heavy freight.