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What is the appeal of reactionary gender movements online? Here we examine how people engage with the so-called “manosphere,” a network of online groups that promote masculinity, misogyny, and oppose feminism. Drawing on semi-structured interviews with 17 participants of The Red Pill, a masculinist forum on Reddit, we analyze The Red Pill as a structured “toolkit” providing morally clear answers to participants going through “unsettled” forms of insecurity. Specifically, we delineate three aspects of The Red Pill that make it appealing to participants: 1) the connection between personal difficulties to perceptions of a broader societal crisis (“the decline of the West”); 2) claims of epistemological superiority (“it’s science”); 3) the emphasis on individual illumination and transcendence (“a hero’s journey”). The Red Pill emerges as a sensemaking toolkit positioning its followers as enlightened and “brutally realistic” observers of a society in turmoil, shaping how they understand gender and sexuality. We conclude by discussing the ramifications of these findings for the study of online radicalization dynamics.