The current study explores the role of coping styles as a predictor of poor psychological health among adolescent offenders. It presents the first study to compare young and juvenile offenders. Two hundred and three male offenders took part: 108 young (18-21 years) and 95 juvenile (15-17 years) offenders. All completed the General Health Questionnaire (GHQ-28) and a revised version of the Coping Styles Questionnaire (CSQ-3). Young offenders reported using emotional, avoidant and detached coping styles more than juveniles. They also reported more overall psychological distress than juveniles, with a trend to report increased depression, anxiety and insomnia. For both young and juvenile offenders, emotional coping predicted increased psychological distress. This was consistent across different symptoms (i.e. somatic, anxiety and insomnia, social dysfunction and severe depression). For young offenders, rational coping predicted a decrease in overall distress and was found across all symptoms. For juveniles, although detached coping predicted a decrease in overall psychological distress, across symptoms it only predicted social dysfunction. Increased rational coping was also found to predict decreased depression for juveniles. The study highlights differences between young and juvenile offenders regarding coping styles and how this relates to psychological distress. It highlights the complexities of trying to understand the coping-health relationship in a prison setting and asks if such settings are increasing the potential for adolescents to over-use coping styles that may not be the most effective.