Drawing on data from white-collar inmates in a United States Federal Prison, this article explains what causes individuals to commit misconduct. Flawed intuition captures the consistent pattern of instinctive, muddled logic by individuals who are influenced by a toxic mix of individual behavioral triggers, organizational context, and the wider industry environment. Combined with limited reflection and/or discussion with others, flawed intuition captures how people cross legal lines owing to a system where factors at multiple levels are working in tandem. This article provides practical recommendations for what can be done to prevent it.