Psychosocial stress is consistently found to promote initiation, intensification, and relapse in drug abuse. It would, therefore, be desirable to identify characteristics of offenders who are at heightened risk for stress-induced exacerbations of addictive behavior. In this cross-sectional, correlational, interview study, 500 clients of two Kentucky drug courts averaged 30 years of age and were predominantly male, White, employed, high school educated, single, and adjudicated in small- and medium-size cities. Five independent correlates of greater subjective stress emerged in stepwise multiple regression analysis (R2 = .395): use of escape-avoidance coping, positive reappraisal coping (inversely associated), more negative life events, better self-rated health (inversely associated), and access to social support related to work problems (inversely associated). Treatment interventions emphasizing effective coping styles and building of social support as well as managing of negative life events and perceptions of health may serve to lessen subjective stress and its consequences in drug-abusing criminal populations.