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This qualitative multiple case study sought to explore the unique ways near-peer mentors serving in three different public high schools support historically marginalized students to address and overcome informational and psychological barriers to college. Data and analysis indicated near-peer mentors utilized instrumental mentoring tools to support student informational needs and relational mentoring tools to emotionally support and push students along the complex path to college. Mentoring and relationship tools expanded on traditional notions of social and cultural capital and illustrated the importance of critical forms of capital often necessary for students from low-income, first-generation college, and/or underrepresented minority backgrounds to successfully aspire to and access college.