In the 1890s a small group of Japanese men settled in a Pacific Island group of Truk (today called Chuuk, located within the federated states of Micronesia). The settlers, who found home in several of the islets surrounded by one of the world’s largest coral reef lagoons, arrived a few decades before the islands became occupied by the Japanese navy and eventually went under Japanese colonial rule with the mandate from the League of Nations in 1920. These earliest migrants had lost their privilege and financial base in the recent regime change in Japan. They are often seen as a pioneer of Japan’s southward imperial expansion, but a closer look reveals that the core of their activity was the export of copra in exchange for contraband firearms. They managed to carry out this trade due to the access to firearms in Japan as well as the kinship network that they forged with Trukese Islanders and other settlers from Europe. By examining the economic and sociocultural background of this copra-dynamite trade in Truk, this paper tries to show how entrepreneurship by migrants could be conditioned by global flows of technological innovation and the conditions of the migrants’ home country.