Education ministries in the Caribbean countries have directed considerable attention over the last decade to "solving" the "problem" of boys' underachievement. Rather than considering such interventions, our central concern in this paper is to revisit debates about the interpretation of the issue, to explore whether boys' underachievement is indeed a "problem", in the sense of both an empirical reality and an issue requiring political attention. In this paper, we explore contestations over the reality and complexity of educational underachievement and whether this relates to broader political-economic marginalisation (or privileging) of boys. We turn then to explore the relationship between material realities and gendered subjectivities. Overall, we argue that boys' underachievement should neither be ignored nor be the exclusive focus of attention and that a move from "boys' underachievement" to a broader analysis of "gender and education" is needed, to place the debate in a gender relational context. (Contains 4 notes and 2 tables.)