This study investigates the aviation activities of Shin Yong-uk, widely regarded as a representative aviation figure during the Japanese colonial period, and elucidates their historical character. Born into an influential family in Gochang, North Jeolla Province, Shin left for Japan in 1921 to acquire aviation skills and returned to Korea in 1927, initially conducting commemorative flights aimed at displaying his personal enthusiasm and pursuit of fame as a pilot. In the 1930s, however, his activities underwent a rapid transformation into politically oriented aviation missions that promoted and publicized Japan’s colonial rule and continental expansion. He actively supported the colonial apparatus by participating in various state-organized aviation events and air-defense drills sponsored by the Government-General of Korea and the Korean Army, and even joined military reconnaissance flights, despite his civilian status. Notably, his 1934 flight celebrating the enthronement of the Manchukuo emperor, his 1935 “East Asian Liaison Flight,” and his 1940 flight marking the establishment of the pro-Japanese Wang Jingwei regime in Nanjing constituted symbolic long-distance operations that legitimized and showcased Japan’s occupation of Manchuria and its invasion of China. In this context, Shin’s aviation pursuits functioned not as contributions to the development of aeronautical technology but as propaganda instruments that justified colonial domination and aggressive warfare. Furthermore, as he later transformed into an aviation entrepreneur and military aviation industrialist, he became increasingly aligned with Japan’s wartime mobilization system in the final phase of colonial rule. Shin’s career demonstrates how an individual in colonial Korea came to follow a pro-Japanese and anti-national trajectory, illuminating the internal logic and structural conditions of collaboration and raising important questions regarding its historical responsibility.