Acquiring English in Puerto Rico involves the perceived advantages of bilingualism in contact with socio-political and economic forces that encourage and constrain the development of a population that is bilingual and biliterate in Spanish and English. Using a mixed design we report the perspectives of 86 experienced English teachers on the Island. Participants generally share an understanding of the complexity involved in acquiring English as an additional language in Puerto Rico at all levels of study. They highlight local challenges of motivation and resources, making suggestions for how successful bilingualism could be supported and enhanced in Puerto Rico and analogous settings.