This article focuses of 13 high school boys' experiences of getting into "trouble" in a former Coloured township high school in KwaZulu-Natal Province. This ethnographic study explored the reasons for boys being considered "troublesome" at school. Data collection included focus groups, semi-structured open-ended individual interviews and non-participant observation. Using the social constructionist perspective of masculinity as an analytical lens, the findings show that these boys' schooling experiences are fraught with anti-schooling, anti-academic and anti-authoritarian attitudes and behaviours. They construct themselves as dominant, unafraid and unwilling to conform to school rules, which brings them into conflict with authorities. While some of the group expressed determination to ameliorate their lives, others dropped out of school prematurely. Teacher attitudes are central to either perpetuating "trouble" or being sensitive to these boys' schooling woes.