Prison wardens manage both external pressures and internal challenges that affect work-related stress. Using data from a national survey of prison wardens, we examined the impact of conflicting job expectations, workload, and job autonomy on work-related stress among prison wardens. The ordered logistic regression results showed a significant and positive relationship between conflicting job expectations and work-related stress. The results also showed a significant and positive relationship between unmanageable workloads and stress on the job. We found a negative and significant relationship between job autonomy and work-related stress, though the relationship was relatively weak. The importance of this study lies in its ability to help isolate factors that affect job stress among prison wardens, which in turn may produce better organizational support, management, and human resources policy to improve conditions for prison wardens, staff, and inmates.