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Life course criminologists study the reasons why, when and how individuals initiate and quit their criminal careers. Until recently, little attention has been paid by criminologists to identify promotive factors that foster individual desistence from crime. Out in the real world of correctional settings, rehabilitative and correctional staff face the daily challenge of identifying the correct array, dosage and sequencing of treatment options that show the most promise in keeping their clients from returning to jail. Given the chronicity and severity of antisocial behavior for some, how should we define and evaluate their treatment success? This paper will explore this question in reference to another chronic, intractable behavior: cigarette smoking. Recent research tells us that the average smoker “quits” about 30 times before successfully giving up the habit. If this is true, how should we appraise the efforts of a chronic offender who seeks to “quit” his or her antisocial career once and for all? This question will be discussed with respect to the task of providing evidence-based treatment to adult male offenders in a correctional setting in Ontario, Canada.