In 1938, when military thinking was shifting from light combat combat to high-speed hit-and-run tactics, the Army issued an order to Nakajima to develop a prototype of the Ki-44 , a high-speed heavy fighter that emphasized speed, climbing ability, and dive performance, at almost the same time as issuing an order to develop the prototype of the light fighter Ki-43.

To satisfy the Army's requirements, Nakajima chose a high-output engine,
deciding on the Ha-41, which had a large diameter but the most powerful engine at the time. This resulted in a thicker nose and drastically reduced wing area to increase speed. Nakajima's unique butterfly-shaped flaps were used on the trailing edges of the wings to improve performance in aerial combat and during takeoff and landing.

Test results showed that pilots who were accustomed to the Type 97 fighter were confused by poor visibility during takeoff and landing and poor stability at low speeds, and the Ki-44 received a bad reputation.
However, in a performance comparison with the Bf-109E and Kawasaki Ki-60, the Ki-44 was superior, so in 1942 it was officially adopted as the Type 2 single-seater fighter and
later given the nickname "Shoki."