Providing preservice teachers in urban settings with authentic educational experiences may be an effective approach in preparing them to teach diverse students. Therefore, this investigation examined preservice teachers' perceptions of mentoring at-risk high school students. Data analysis reflected preservice teachers' positive experiences and their role as future teachers. The social interaction with at-risk students fostered a deeper understanding of the importance of relationship building and helped to clear teachers' negative assumptions about at-risk students. This study suggests that preservice teachers in urban settings may enhance their pedagogical knowledge and course work learning by mentoring at-risk students.