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This article utilizes a combination of the masculinity and intersectionality frameworks to argue that the underachievement of boys occurs in the intricacies of patriarchy, region (rural area), and class culture. The article utilizes data drawn from a qualitative study at two rural institutions in the parish of Manchester, Jamaica, to critically analyze the gendered nexus between boys’ underachievement and educational policies. The low grades merited by boys raise questions of patriarchy in the educational system in which they and their female teachers operate. While the failure of boys is not generalizable to the entire population, underachievement is also located in the mismatch between curriculum and the culture of these boys.