In many cases, the school failure cycle begins in elementary school for students with specific risk factors. Young students with learning difficulties and behavioral problems require a timely and sufficient program to prevent poor school outcomes. After-school mentoring programs are effective in providing meaningful relationships, structure, and academic support, thus mitigating risk factors and improving academic achievement. This case example describes a year-long, cross-age peer mentoring program between high school students identified as gifted and elementary students with risk factors attending adjacent schools with support from a local university. The positive results of this community-based mentoring program include improved academic grades, teacher perceptions, student-rated self-efficacy, and social validity. These results are presented along with implications for practice.