While a great deal of research has examined the form and format of extremist content and the expressions of hate speech that exist within far-right online communities, there has been less attention on why young men, the primary target audience, become motivated to engage with this kind of material. As a corollary, what is also missing from most accounts of radicalisation is a sustained discussion of how discourses of masculinity are leveraged in extremist spaces and how these discourses become part of an overarching system of persuasion, manipulation, and, ultimately, recruitment to extremist organisations. This chapter offers an analysis of data collected from r/The_Donald to examine how discourses of masculinity are exploited as a means of promoting and normalising extremist positions within the community. The chapter also shows how these discourses of masculinity are bound up with race and ethnicity, where particular raced and gendered configurations become valorised as ideal, normative, and desirable. Taking all of this together, I argue that closer attention to the nature of these gendered discourses can help us develop more effective interventions around deradicalization, as well as better informing public education campaigns, particularly those aimed at young men.