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The COVID-19 pandemic rapidly transformed community supervision practices, necessitating the rapid integration of technological enhancements, safety protocols, and policy adjustments. Probation and parole officers (PPOs) had to adapt swiftly, facing an increase in workload, shifting responsibilities, and heightened concerns about personal and public safety. These challenges exacerbated existing stressors in a profession already marked by high rates of burnout and turnover. Using data from in-depth interviews with 56 PPOs, the current study explores three primary research questions: (1) How did working during the pandemic impact PPOs’ mental health?, (2) What were the main stressors PPOs faced while working during the pandemic?, and (3) What personal coping strategies and organizational-level supports did PPOs use to manage mental health challenges? By identifying key factors linked to mental health outcomes, the study offers actionable recommendations for leaders and agencies to enhance support systems and foster positive mental health among PPOs.