While there is a growing presence of trans-Pacific migrant students in the US, relatively little attention has been given to the diversity among them in terms of their everyday experiences and future educational trajectories shaped by different patterns of transnational mobilities and practices. This paper addresses the distinctive educational experiences and needs of transnational Japanese students, temporarily enrolled in US schools accompanying their parents on business appointments from transnational corporations. This institutional ethnographic study examines the strategies that these sojourner students use to negotiate the institutional demands of US high-school life and the way to promote access to tertiary education in Japan. The findings show that, although corporate transnationalism restricts Japanese sojourners' geographical mobility, they still actively construct their futures through the high-stakes strategy of graduating a year early from US high schools. I call this early graduation scheme a gambit because the sojourners sacrifice beneficial opportunities and even risk their graduation itself in the hope of securing a positional advantage upon their return to their home country. The early graduation gambit is analysed through a lens of transnationalism.