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While substantial effort has been devoted to investigating the radicalization process and developing theories to explain why this occurs, surprisingly few studies offer explanations of the micro-situational factors that characterize how extremists accomplish violence. Relying on in-depth life history interviews with 89 former white supremacists, we analyzed the situational, emotional, and moral considerations surrounding white supremacist violence. Overall, we identified a variety of strategies white supremacists utilize for overcoming emotional and cognitive obstacles required to perform violent action. Furthermore, we also identified the callous effect of habitual violence. We conclude this article with suggestions for future research and recommendations for practitioners addressing terrorism prevention initiatives.