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This paper discusses the language learning journey of a Puerto Rican transnational student and the factors that shaped his acquisition of English as a second language and his identity, having moved to California and returned to his homeland. His experiences also portray some of the current ideologies of Island Puerto Ricans regarding English as its regular use is often not received well by non migrants. Puerto Rico has had a socio-political relationship with the U.S. since 1898 when it became a U.S. territory and the movement from the Island to the mainland is part of Puerto Ricans’ everyday reality. Hector’s case reflects the struggles of many other students who constantly move back and forth from the Island to the mainland.