Much of the literature regarding correctional officer job stress and job satisfaction has examined the roles of organizational and demographic variables. This study examined the relationships among generation, job stress, and job satisfaction of correctional officers in a southern prison system. Hierarchical multiple regression was used to assess the relative impact of demographic variables and generation on job stress and job satisfaction, as well as the impact that stress and satisfaction have on one another. Results indicate that generation membership and job stress significantly shape correctional officers’ perceptions regarding job satisfaction. Conversely, gender and job satisfaction significantly influence job stress. The authors recommend that further research on generational differences among correctional officers be undertaken to assess the overall impact that generation has on employee perceptions of correctional employment.