(1) Background: Correctional Officers show signs of adverse health early in their careers. We evaluated the impact of a one-year peer health mentoring program for new officers based on a Total Worker Health® approach; (2) Methods: Cadets (n = 269) were randomly assigned to a mentored or control group. Cadets in this mixed methods design completed physical assessments, and surveys at three time points to assess demographics, health, mentoring, and workplace variables. Physical testing included several health markers. Surveys and physical data were analyzed as repeated measures. Regression analyses were used to analyze the relationship between mentoring characteristics and outcomes. A semi-structured interview of mentors was analyzed qualitatively. (3) Results: Higher mentoring frequency was associated with lower burnout. Health behaviors and outcomes declined over time in all groups, but mentees displayed slower decline for body mass index (BMI) and hypertension compared to controls. (4) Conclusions: A continuous peer health mentoring program seemed protective to new officers in reducing burnout and also declines in BMI and hypertension. Short-term physical health markers in younger officers may not be an index of psycho-social effects. A participatory design approach is recommended for a long-term health mentoring program to be both effective and sustainable.
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