This paper draws on Matthew's story to illustrate the conflicting discourses of being a boy and being a student. Matthew is 12 years old and in Grade Six, his final year at Banrock Primary (a K-6 Australian State School). School is far from a happy place for Matthew--his tearful accounts of his combative relationships with his peers and his teacher highlight his emotional distress. The paper's analytic focus draws attention to some of the ways Matthew's harmful storylines of hegemonic masculinity are made possible through, in particular, his teacher's gendered philosophies and her strategies of individualism and control. In this regard, Matthew's story provides insight into the potentially counterproductive realities of teacher practice in relation to addressing issues of masculinity within the school environment. Against this backdrop, the paper stresses the importance of teachers drawing on a sound research-based framework of gender knowledges that can illuminate how masculinities are constructed, regulated and, indeed, transformed through the power relations of everyday social practice, including teacher practice. (Contains 1 note.)