This study examines the process of the transition from high school to work among Japanese youth. It focuses on the role of high schools in shaping the unequal distribution of the four outcomes of their first jobs: the timing of job entry, employment status, firm size and whether the job was first preference. The empirical evidence of this study suggests that Japanese high schools continue to play an active role in matching students to jobs, and that there is no apparent decline in the use of the school-mediated system or the effects of using such a system on labor market outcomes. Contrary to the observations by the Japanese mass media and some academics, the idea of the breakdown of the school-mediated transition to work does not receive much empirical support.