In this paper, we examine the efficacy and relevance of constructivist pedagogy within the Jamaican schooling and educational contexts. We recognize that it is an educational topic that has received a fair amount of attention in Jamaica, one which has been discussed and written about by numerous scholars and educators who have focused extensively on areas of curriculum, teaching, and learning (Down, 2008; Evans, 2006; Figueroa, 2010; Gentles, 2006; Jennings, 2007). Alongside these scholars, we discuss the challenges inherent in implementing constructivist pedagogy in present-day Jamaican schooling. We argue that implementing and sustaining constructivist modes of teaching and learning in Jamaican schools pose particular challenges, given the persistence of behaviorist pedagogy, the reluctance to acknowledge and use the Jamaican language—the first language of many students, the emphasis placed on standardized testing as the definitive form of student assessment, and the overcrowded and under-resourced classrooms.