Drawing from a one-year qualitative research study, this article explores the transnational lives and experiences of three young women and their little sisters in New York with close ties to the Dominican Republic. Using ethnographic research methods—life history interviews, focus groups, participant observation, and document analysis, I examine how transnationalism shapes immigrant Dominican families, from the perspective of adolescents in particular. I also share findings from the schooling experiences of the transnational youth in both the Dominican Republic and the U.S. However, the most compelling findings address language learning that takes place in and out of formal educational settings. Here, findings point to the injustices and ironies bilingual immigrant youth withstand in their Spanish-as-a-foreign-language classes. The insights of the youth point to immediate policy recommendations that could improve the U.S. schooling experiences of transnational Dominicans.