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With the growing efforts to address the opportunities gaps for low-income and minority youth, mentoring has been part of the dialogue to ensure all students complete their education beyond high school (Hurd, 2016; Moore 2016). The purpose of this mixed-methods study is to explore a regional mentoring program’s impact on students who have been referred due to problems with behavior, attendance, and/or grades. We draw on Stanton-Salazar’s (2011) framework of institutional agents to explore students’ perceptions of their mentoring relationships. This study has implications for school practitioners, community partners, school districts, and researchers on how to build connections between theory, practice, and policy to ensure all youth have an opportunity to learn and develop positive relationships with adults in schools.