ABSTRACT The relationship between probation/parole officers (POs) and their clients under community supervision plays a crucial role in successful reintegration. This study investigates how POs’ communication orientations influence relationship quality and the occupational self-efficacy of women impacted by the justice system, drawing on family communication patterns and self-efficacy theories. A public dataset of 402 women on probation or parole in Michigan, USA was recruited using a cross-sectional snowball sampling approach. Regression analyses revealed that POs’ communication orientation predicts women’s occupational self-efficacy and relationship quality. Equally important, caring and trust mediate the positive relationship between POs’ conversation orientation and women’s self-efficacy in their job-related abilities, while trust also moderates this relationship. These findings have important implications for POs, counselors, and educators in correctional systems, and inform future research directions on PO-client relationships and career development for justice-involved women.