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Research on criminal desistance has greatly increased in recent years. Scholars have identified a number of role transitions (e.g., marriage and employment) as potential explanations for desistance. Despite this attention, less empirical inquiry has been devoted to uncovering why role transitions appear to reduce offending. Relatively little is known about the causal processes through which desistance works. In fact, there are many theoretical propositions that attempt to explain how various role transitions influence desistance, including the development of “stakes in conformity,” changes in routine activities, and cognitive shifts. Using longitudinal data from a sample of serious adolescent offenders from the Pathways to Desistance study, the current study tests the aforementioned intervening mechanisms by which role transitions may lead to the cessation of offending. Implications for theory, research, and policy are discussed.