As the U.S. teacher shortage continues to worsen, large, urban districts have turned to hiring teachers from abroad, including countries like Spain, Mexico, and the incorporated U.S. territory of Puerto Rico. However, several researchers in the field of have pointed out to the unexamined complexities of hiring Latin American and Spanish teachers to fill in vacancies in U.S. bilingual classrooms. Although these teachers are often what some deem a linguistic match, differences in class, culture, and migratory experiences should send, in the least, a cautionary message to school districts, oversea recruiters, and school administrators. In this essay I discuss and problematize these complexities and offer recommendations for researchers, district personnel, and teachers.