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This study examined the impact of workplace factors—such as officer shortages, officer culture, job constraints, and leadership effectiveness—on correctional staff stress and job satisfaction. Specifically, it explored how job-related emotional stress mediates the relationship between workplace conditions and job satisfaction and whether effective facility management can buffer against these negative effects. Self-reported survey responses from a large sample of personnel within the Florida Department of Corrections (n = 9,656) were analyzed using a moderated mediation path analysis. Findings suggest that weak officer culture, staffing shortages, and job constraints significantly contributed to emotional stress and, in turn, reduced job satisfaction. Emotional stress was identified as a key mechanism through which workplace conditions influence job satisfaction, mediating the relationship between work stressors and job satisfaction. However, perceived effective facility management moderated these relationships, mitigating the adverse effects of emotional stress on job satisfaction. The findings suggest that there is a need for correctional institutions to address staffing shortages, strengthen officer culture, and improve leadership training to mitigate workplace stressors. Policies that aim to invest in leadership development programs and organizational interventions that foster workplace cohesion can enhance institutional stability and reduce operational disruptions linked to high turnover rates.