This dissertation research showcases six ethnographic case studies that focus on the experiences of Puerto Rican transnational youths and their families upon returning from the US to Puerto Rico. Puerto Rico is a remarkable setting to study transnationalism because of its particular historical and sociopolitical relationship with the US, which grants Puerto Ricans citizenship and thus ease of movement, while retaining a strong attachment to the Island. It can be argued that Puerto Ricans define transnationalism, being simultaneously insiders and outsiders to the US national scene. The youths involved in these dynamics learn to navigate different educational and social settings on the Island and the US. Factors like language and the educational contexts are highly influential in the students' lives and their educational outcomes. The study was conducted over a period of seven months in two public schools in Puerto Rico. The data were collected through interviews, classroom observations, and home visits with return migrant students, their parents, and their teachers and school staff. The combination of these data collection methods and the variety of participants, provided a nuanced portrayal of the nature of their transnationalism and the social and educational experiences of the families in and out of the school context.

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