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The immigrant population in Japan reached the historic high of four million during 2025, following continuous growth since the 1990s. As Japan emerges as an “immigrant nation,” the issue of integration poses a critical challenge. Japanese language proficiency is widely considered the primary vehicle for socioeconomic mobility and social inclusion. This paper examines the case of “evening junior high schools” (yakan chūgaku)--historically marginalized institutions established in the postwar period as a safety-net for public education for adults beyond compulsory school age. Over the last two decades, these schools have undergone a significant demographic shift, with foreign-born students currently comprising the vast majority of the student body. In response to the linguistic needs of these students--many of whom are employed in low-skilled, low-wage jobs--yakan chūgaku have modified their curriculum towards instruction in the Japanese language. Based on field observations and interviews at several schools in the Tokyo metropolitan area, this study finds that while yakan chūgaku function as important sites for developing Japanese proficiency, immigrant pathways to upward mobility remain limited. Following graduation, many immigrant students move on to senior high schools. The majority are channeled into part-time and lower-level schools where academic rigor is lacking and where high dropout rates hinder advancement. The present study finds that yakan chūgaku function as sites for acculturation while perpetuating the marginalization of less-privileged migrants. Immigrant educational trajectories appear to be shaped by existing school stratification, which in turn structures socioeconomic outcomes and the possibility of upward mobility.