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Recognizing the need for a more comprehensive approach to working with justice-involved women, the Multnomah County Department of Community Justice, Women and Family Services Unit created the Women’s Reentry Assessment, Programming, and Services (WRAPS) supervision model. WRAPS is an enhanced wraparound, gender-responsive, and trauma-informed support model of supervision. A unique component of the WRAPS model is the integration of Community Health Specialists (CHSs) who work alongside probation officers. To our knowledge, the inclusion of CHSs within the realm of community corrections has not been previously attempted in the U.S. A randomized control trial, mixed-methods outcome evaluation was conducted to examine the effectiveness of the WRAPS model in comparison to ‘gender-responsive supervision as usual.’ For the qualitative component of the study, semi-structured interviews (n = 17) were conducted with treatment and control group staff and clients. Thematic analyses of the interviews found strong support for the continuation of gender-responsive practices and the WRAPS model. Additionally, there was evidence supporting the CHS role; clients and probation officers viewed the CHS role as highly impactful in addressing women’s responsivity needs and supporting women’s success on supervision. Recommendations and considerations based on the qualitative findings will be discussed.