Drawn from my current book project that examines the history of the tension between nativism and demand for foreign labor in the United States, this presentation explores the social, legal, and diplomatic contexts in which Japanese migration to North America was contested at the turn of the twentieth century. An increasing number of the Japanese migrated to North America, often via Hawaii, during the final decades of the nineteenth century, in part because of the growth of the transnational business of migrant labor importation, a development stimulated by constant demand for labor in North America. The arrival of Japanese laborers provoked intense racial animosity among white residents who regarded the Japanese as unfree, servile people equivalent to slaves and as threats to their employment. Pressured by white workers, the US Bureau of Immigration attempted to restrict Japanese labor immigration, but its efforts were constantly plagued by labor contractors’ and shipping companies’ strategies for law evasion. While the tension between restrictionists and parties who wanted Japanese labor shaped the course of immigration law enforcement on the ground, the Japanese and US governments sought ways to reduce Japanese labor immigration without hurting mutual diplomatic interests in maintaining friendly relationships. By analyzing the activities and languages of importers of Japanese laborers, white restrictionists, immigration officials, diplomats, and finally Japanese migrants, this presentation illuminates the political landscape of Japanese border crossing in North America.