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Juveniles transitioning to the community from a congregate care setting face several challenges. Mentors can be a vital source of support and guidance during this transition, but there is a lack of understanding regarding the characteristics and perspectives of these unique matches as they relate to individual and match outcomes (Hanham & Tracey, 2017; Chan & Henry, 2014). Using a mixed methods approach, this study seeks to explore various aspects of juvenile mentoring relationships. Identifying the mentor’s focus, experience, and attitudes along with the mentee’s, are important in considering the qualities that influence positive match outcomes (Spencer, 2012). The role of gender, race, ethnicity, and age are also important to consider for the success of juvenile reentry matches.