In recent years, an increasing number of historians have studied the construction of masculinity in various Middle Eastern contexts. Yet, the focus has generally been on the modern middle-class. Departing from the dominant trend, this paper explores the intersection between masculinity, class formation, and technology by examining the construction of working-class masculinity in Iran during the early Pahlavi period, with a particular focus on workers of the transport sector. Transport infrastructure developed tremendously during the second quarter of the twentieth century. In addition to a highway network, the Trans-Iranian Railway connected the Caspian Sea with the Persian Gulf via Tehran. Coterminous with this development was the increase of intercity bus services and trucks that transported people and goods. Particularly during WWII, the occupying Allied forces relied heavily on Iran’s transport infrastructure to carry lend-lease materials from the Persian Gulf to the Soviet Union. This development created an acute need for the railway crew, truck drivers, and various other workers of the transport sector, many of whom were employed directly or indirectly by state institutions or the Allies. This paper asks: How did this largest workforce in Iran outside the oil industry develop a distinct type of working-class masculinity in the context of modern state formation under Reza Shah Pahlavi (r. 1925-41), the Allied occupation during the war, and its immediate aftermath in the late 1940s? How was their masculinity constructed in relation to competing ideals of masculinity? What role did technology play in the process? Using archival documents of the American Persian Gulf Command and publications of the Iranian Ministry of Roads and the Iranian Railway Organization, this paper argues that the masculinity of transport workers was based on their technological ability to operate and fix the automobiles and locomotives, their financial ability to feed their nuclear families, and their willingness to sacrifice themselves to operate the transport system in order to end the war. These qualities separated them from modern middle-class men, the “ignorant masses,” women, and even other working-class men. The end of the war and the subsequent waves of layoffs exacerbated their crisis of masculinity by the eve of the oil nationalization movement that began in 1951 under the leadership of Mohammad Mosaddeq.