As communities of immigrant families gather in the low-income neighbourhoods of Tokyo and neighbouring cities, Japanese teachers face new challenges as well as the stigma of classrooms for immigrant children. Within the intricate politics of assignment in Japanese school districts, teachers and administrators can find themselves with students who are barely acknowledged and poorly served by mainstream Japanese schools and other community services. The interviews with teachers, principals, immigrant translators and other cultural intermediaries as well as numerous school visits focused on the ways in which teachers had been required to interrogate their pedagogies, practices and prejudices in order to be effective teachers of low income and immigrant youth. The results reveal strains in the lives and careers of teachers who work with marginalised youth in Japan and are addressed within a critical view of how Japanese schooling is responding to the needs of an increasingly heterogeneous urban population.