This chapter explores the intersection of trauma, masculinity and offending behaviour, arguing that many justice-involved males experience a ‘deprivation of alternatives’. It investigates how restrictive norms of traditional masculinity—emphasising strength, emotional suppression and aggression—limit the ways boys and men respond to trauma. Through the lens of gendered socialisation, the chapter examines how shame, silence and internalised stigma can redirect emotional pain into violence or criminal behaviour. It further highlights the exacerbation of these dynamics within prisons, where hypermasculine environments intensify trauma. The chapter concludes by arguing for trauma-informed, gender-responsive interventions that expand emotional expression and provide pro-social alternatives for coping.