The Boy Scout movement was founded in England in 1908 based on the principles of courage, discipline, and fair play in sports. By 1918, it had expanded to become a worldwide youth movement that taught patriotism and deference to the established social and political order. As part of colonial education and the youth movement, the Boy Scout movement expanded into Mandate Iraq and colonial Kenya in the 1920s and gained immense popularity in the 1930s. Based on British colonial archives, Iraqi government documents, and the Kenyan Boy Scout Association’s handbook, this paper uses the concept of masculinity to examine the Boy Scout movements in Iraq and Kenya. In its discussion, it examines how these movements tried to impose hegemonic masculinity and how native scouts appropriated the notion of masculinity to resist British colonial rule. I argue that while the Boy Scout movements in Iraq and Kenya instilled normative British masculinity among Iraqi and Kenyan youth, Iraqi and Kenyan scouts applied the movement’s laws and norms to their own political, social and economic advantages. In Iraq, scouts combined the Boy Scouts’ idea of youthful masculinity with militarism to construct their ideals of manhood and patriotism. In Kenya, scouts reinterpreted the Boy Scout Law and appropriated the Boy Scout uniforms to build their prestige and privileged status within their community. In both contexts, the Boy Scout movement provided a training ground for the formation of Arab and African nationalisms which served to destabilize the British form of hegemonic masculinity through anti-colonial movements. This study contributes to the scholarship on gender and empire by demonstrating multiple forms of transnational masculinity through divergent indigenous responses.