This article examines international transactions related to steam locomotives at the beginning of the twentieth century while focusing on Japanese trading companies. In particular, it considers in detail how Japanese trading companies acquired the knowledge and know-how of locomotive trading to carry out their business transactions through a case study of Okura & Co.'s New York branch office. The analysis highlights the following three factors that supported Okura's locomotive trade in New York: first, the company took advantage of business opportunities by collecting information through networks of Japanese contacts in New York and local experts; second, it utilised social and technological infrastructure, including international communication lines, transportation, and financial systems, as key fundamentals of its overseas activities; third, a former oyatoi (hired foreigner) played a critical role as its consulting engineer. In particular, the overseas activities of Japanese trading companies drew heavily on formerly hired foreign engineers, whose technological knowledge and networks became an essential route of knowledge transfer in cross-regional commercial management. These will contribute to the evolution of history related to the starting points of global activities of Japanese trading companies.