Research on general strain theory has demonstrated the impact of strain on decisions to engage in crime and delinquency. However, people differ in their responses to strain and only some resort to crime or delinquency. There remain gaps in our knowledge of when, and under what conditions, individuals will react to strain with offending behavior. We rely on interviews with 40 incarcerated men to understand how they cope with specific prison strains, and why they make such coping choices. We find considerable variation in inmates’ coping responses. They use a variety of coping strategies—behavioral, cognitive, and emotional—and only some of these strategies involve offending. Our findings indicate that responses to prison strain are partly a function of past experience with strains, including prior experimentation with coping techniques. Results highlight the unfolding nature of the coping process and expose factors that deserve further attention in tests of GST.