In the US and UK, Black fatherhood has long been steeped in narratives of pathology. Despite the promotion of nuanced understandings of Black fatherhood in recent scholarship, research on Black fathers' positive engagement with urban schools remains remarkably limited. This article adds to the literature by highlighting the strategies Black Caribbean fathers deploy to challenge assumptions about their identities and involvement. Based on 20 in-depth interviews with 10 Caribbean immigrant fathers in London and New York City, the analysis rendered utilises Critical Race Theory to highlight how some Black men attempt to counter racial subordination through masculine domination, particularly when engaging with white female teachers. The empirical analysis reveals that groups of Caribbean immigrant fathers draw on three common strategies to offset negative stereotypes about their engagement and assert their masculinities--namely, distinctiveness, deference and dominance.