Providing authentic encounters with secondary students may be a way to provide a realistic image of students' academic challenges, and enhance preservice teachers' skills, knowledge, and dispositions to better address the needs of their future academically, linguistically, socially, and culturally unique students. The purpose of our study was to examine preservice teachers' experiences in mentoring at-risk high school adolescents. Specifically, we sought to identify the connections to pedagogy associated with their mentoring experience. Major findings generated five themes: (a) relationship building, (b) academic immediacy, (c) embracing a professional lens, (d) a student-centered pedagogical philosophy, and (e) self-efficacy.