Educators continue to struggle with how masculinities are performed and regulated in spaces of learning. In a time of rapid social change, there is a renewed impetus for gender justice reform in schooling, though these approaches themselves remain a shifting picture. Adding a new layer of complexity, we are now witness to educational policy recommendations around surveillance which are designed to counteract boys' and young men's vulnerabilities to be radicalised into the misogynies of the 'manosphere'. These recommendations exist despite limited research and significant gaps in our understanding regarding both the manosphere as well as the emotional lives of young men. The article intentionally shifts the conversation from reactive surveillance in schools to educative gender justice approaches. We focus, in particular, on the significance of 'pedagogic discomfort' in terms of fostering gender transformative dialogue which is critical of ideas associated with the manosphere. We consider how a constructive dialogue might be fostered with a particular focus on pedagogies that recognise the emotional intensities of gender justice work.