Despite the widespread concern regarding young people's wellbeing, the interaction between gender and mental health appears to be generally overlooked within education and is more commonly focused on concern about rising figures of female mental health. The absence of discussions around gender is surprising, given the ongoing debate regarding the impact of masculinity on men's emotional expression and the increasing encouragement for men to talk more openly about their mental health. The paper will present a small-scale study that explored how boys' behavioural and mental health difficulties are constructed in the discourses employed by teachers and boys themselves. The findings highlight the complexity of discourses around boys' behaviour and mental health which are inextricably tied to constructions of masculinity. This paper will critically consider these findings within the wider debate about masculinity and emotionality, before considering implications for boys in schools and for educational practitioners.