School-based mentoring (SBM) programs have emerged in response to the chronic academic failure of many at-risk youth. Students encountering poverty, familial instability, poor health, and/or exposure to violence and mental health issues are at greater risk of academic failure. The pressures bearing down upon the most vulnerable students foster emotional and behavioral challenges that manifest in the learning environment, ultimately hindering academic achievement. Youth mentoring is one response to this epidemic. This conceptual article will evaluate the key components of SBM. Program interventions, outcomes, and limitations will be discussed. The concept of multisystemic mentoring (MSM) will be introduced as a viable expansion of SBM programming that offers a wraparound intervention for schools. The four domains of MSM will be introduced--school, family, peers, and community--and suggestions for program development will be provided. This information is valuable for school social workers and educators interested in bridging the gap between education systems and the holistic needs of traditionally marginalized students.