Using an expectancy-value framework, the present investigation is the first to explore the generality of this theorizing and research in the emerging regional context of the Caribbean. Given high underachievement in the Caribbean region, we addressed the need to better understand the role of engagement in students' academic motivation and achievement. A total of 585 year 6 to 9 students from five Jamaican schools responded to a survey assessing their motivation milieu (academic expectations and values held by their parents, teachers, and peers), their self-motivation (expectancies and values), behavioral engagement (class participation, homework completion, school absenteeism), and their academic achievement (in mathematics, language arts, and science). Structural equation modeling showed that (a) students' own motivation was influenced by their motivation milieu, and (b) students' behavioral engagement significantly mediated the relationship between their motivation and their academic achievement. Findings confirm the generality of behavioral engagement effects among students in the developing Caribbean region and represent a novel contribution to the study of developing and emerging educational contexts more broadly.