Naturally-occurring mentoring relationships with caring, nonparental adults can provide critical support to underrepresented students during the transition to college. The current study sought to examine the nature of underrepresented students' relationships with natural mentors during their first three semesters in college. Results revealed that participants perceived greater relational closeness with natural mentors who were extended family members or family friends compared to natural mentors from other categories (e.g., natural mentors who were teachers). Moreover, natural mentors who were extended family or family friends provided greater levels of emotional, appraisal, informational, and instrumental support to students relative to natural mentors who were former teachers or other school staff. Natural mentors who were college faculty or staff provided more informational support than natural mentors who were family or family friends. Findings have implications for understanding intergenerational mentoring relationships that may promote resilient outcomes among underrepresented students transitioning to elite, predominantly white colleges and universities.