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As transnational movement between the Dominican Republic and United States continues into a new generation, it is important to understand how such movement affects the lives of transnational youth. Unlike adults who choose to move transnationally for a variety of reasons (many times in economic risk-reduction) youth rarely have the power to determine their transnational reality, rather, the adults in their lives choose it for them. Regardless of who controls the power of decision, transnational movement has a great effect on youth especially in their formation of identities and their academic experiences. The following study, which includes an overview of the field of transnationalism, I examine the effect transnationalism has on the lives of four Dominican case-study participants who were also my former students. Through their stories (and my teacher-reflections) I provide evidence that further research on multi-generational transnationalism is necessary, especially to understand and address the complex needs these transnational students have in classrooms in both the sending and receiving countries.