Recidivism rates for previously incarcerated offenders are very high. These rates can be partially attributed to various barriers to reentry, including unemployment, financial difficulties, mental illness, and many others. In question is whether individual coping style could act as a significant predictor of recidivism. This study examines the relationship between individual coping style, as measured by the CISS:SSC, and negative reentry outcomes, specifically arrest, reincarceration, and parole failure, utilizing a cross-sectional study of previously incarcerated inmates residing in halfway houses. Results from this study indicate a relationship between emotion-oriented coping and negative reentry outcomes, in that individuals with a mental illness and emotion-oriented coping style are more likely to be arrested, non-white individuals with an emotion-oriented coping style are more likely to be reincarcerated, and individuals with an emotion-oriented coping style are more likely to experience parole failure. Policy implications and directions for future research are discussed.