This research explores why the boys academically underachieve in Turks and Caicos Islands (TCI). The research is set against the backdrop of the ongoing global debate on boys’ failings in education - a phenomenon of serious national concern in TCI and the wider English-speaking Caribbean. TCI has not undertaken any previous research on the causes of the educational failings of their boys. This research seeks in part to remedy this deficit. Five (5) research questions are formulated and answered. They focus on the effect of the following on boys’ academic underachievement (BAU), namely: the negative stereotyping of boys; the predominance of women in education; masculinity (and the boys’ negotiations of it) and past historical events such as slavery and its legacy of absentee fathers. These are found to have caused BAU in TCI, thus largely confirming previous research findings on the causes of BAU in the Caribbean. The literature review, among other things, outlines and engages the main theoretical concepts by which BAU has been debated and explained. Aspects of these theoretical concepts are interrogated through the lens of post-colonial theory and Fanon’s psycho-political concept, both of which constitute the theoretical framework of this research. For the purpose of data collection, qualitative research methods of interviews, peer dialogue, focus group and ‘second’ literature review have been chosen. This choice was informed by my world view and positionality. Psycho-political thematic analytical tool has been deployed in the data analysis. This enabled ‘beyond the surface’ interpretation of the data. Although this research confirms previous research findings, it does so from a fresh theoretical perspective. This perspective looks beyond the boys for their failings and looks to external historical and political forces such as slavery and its deleterious legacies of generational impact. In this sense, this research makes a contribution to knowledge by adding theoretical depth and breadth to our understanding of BAU. It also makes recommendations to inform a better articulated boys’ education policy and practice in the Turks and Caicos Islands. These recommendations include reframing the BAU question from ‘why are the boys failing’? to ‘why are we failing the boys’?