In recent years, gender dynamics in education in the English-speaking Caribbean have undergone significant shifts. On the one hand, educational access, retention and attainment by girls have improved significantly and should be celebrated. On the other hand, retention, completion and attainment by boys appear to be slipping. The question at the centre of these changes is whether the decline for boys is relative (boys only appear to be declining because girls are doing so much better) or real (fewer boys are reaching their potential than was the case in the past). To explore this question preliminary data from a larger qualitative project on Caribbean masculinities were examined. As a result of this work new perspectives have emerged that may help to explain boys' changing educational achievements. In the past, academic excellence was largely, if not entirely a male domain. However, with education increasingly becoming 'common ground', boys are left with fewer opportunities to establish their gendered identity through education; and academic achievement furnishes those needs less readily. In contrast, fundamental biological differences means that physicality has been preserved as a way of asserting masculine difference, and the 'outdoors' remains boys' territory. In the Caribbean and elsewhere, outdoors physicality seems to have gained pre-eminent importance for developing a boys' identity. While this 'retreat to physicality' may well benefit sporting achievements, there are also important negative consequences. Opportunities to prove one's gender identity through physical dominance are increasingly driven towards hard, physical, risk-taking, hyper-masculine, sometimes antisocial acts including bullying, harassment, crime and violence. Meanwhile, boys who do achieve in academic pursuits are at risk of being considered 'suspect' by their peers and of becoming the subject of gender taboos. This includes boys who show a preference for reading, who regularly reported receiving homophobic criticism, perhaps the deepest of all masculine taboos. The research also sheds light on HIV risk. Through the twin mechanisms of obligation and taboo, a wide range of risks, including sexual risks have become resiliently embedded in the social fabric and are, as a result, highly resistant to change. I call this phenomenon 'social embedding'. Social embedding has its impact by way of gender roles, peer group dynamics, stigma and taboo and socioeconomic factors. To address social embedding and to achieve sustained, widespread results, strategies for producing grassroots social change with embedded behavioural outcomes will be required.