Introduction Individuals in the U.S. criminal justice system now represent over 12% of all current U.S. smokers. With smoking banned in most U.S. jails and prisons, the cessation focus for this population has shifted to individuals who are under community correction supervision (e.g., probation, parole). The aim of this study was to examine predictors of successful smoking cessation among criminal justice individuals supervised in the community. Methods Five hundred participants under community corrections supervision were randomized to receive either four sessions of smoking cessation counseling or no counseling in conjunction with 12 weeks of bupropion treatment plus brief physician advice to quit. Logistic regression analyses examined associations of smoking variables with medication adherence and successful abstinence. Mediation analysis evaluated the indirect effects of medication adherence on smoking abstinence. Results The strongest associate of medication adherence was previous use of bupropion, while the strongest associate of smoking abstinence was medication adherence. Mediation analysis indicated that previous use of bupropion indirectly increased cessation rates through the pathway of increased medication adherence. Conclusions These results highlight the importance of medication adherence for smoking cessation among community corrections smokers. Providing exposure to medication may be a promising intervention to increase medication adherence and subsequent cessation rates in this population.