Over the last two decades, a focus on challenging and transforming dominant forms of masculinity and engaging boys and men towards gender equality and healthy masculinities has permeated South African social and health sciences and the humanities. This focus on men and boys has also been evident in intervention and activist work. However, the turn to boys, men and masculinities has not gone without resistance, contestation and contradictions. A range of localised and global realities has frustrated much of the enthusiasm for rapid, sweeping and concrete changes regarding gender justice and the making of progressive masculinities. Among the discursive and material forces that oppose work that engages boys and men are those to do with income-related issues, race and racism, cultural traditions and gender itself. Because of this, it is contended that engagement with boys and men needs to consider not only gender but also economic inequality, poverty and unemployment, divisions created by race, and struggles around tradition. This paper discusses these forces that undermine and counteract work with boys and men and how we might work through resistance in engaging with men and boys.