This article explores one key aspect of staff/prisoner relations—the role of fairness—as a predictor of young people’s adjustment to pre-trial detention. Participants were one hundred thirty-seven 13- to 19-year-old youth held in one of five secure youth detention centers in southern Ontario, Canada. Findings from this study suggest that youth with high levels of pre-existing vulnerability and prison stress who were more fearful and felt that staff did not treat them fairly were more likely to experience poorer adjustment. Fairness would, therefore, appear to be an important component of staff/prisoner relationships and of adjustment while incarcerated.