Extant literature exposes the inordinate stress placed on urban school personnel and their students. While they both persevere through innumerable symptoms of a struggling educational system, both parties are expected to perform at their maximum during the teaching and learning process. This chapter, which is based on the well-being of boys and young men of color (BYMOC), discusses the effects of a community-based ecosystems approach. A community-based ecosystem is the social environment of a group of people that accurately represents their culture and includes parents/guardians, siblings and other family members, neighbors, school personnel, policymakers, and other people who make up the group’s “community.” A community-based ecosystems approach is an interconnected process of acknowledging and addressing the need for stress management, wellness, self-empowerment, and healing strategies of the BYMOC’s social environment. Data from the study on which this chapter is based were collected from 2436 youth, educators, school district personnel, parents/guardians, youth practitioners, and community members over 3 years. The study revealed a strong correlation between targeted interventions focused on the cultivation of a healthy ecosystem for both school personnel and boys and young men of color and the increased ability to improve school dynamics and learn skills to reduce the negative effects of stress and trauma. Assessment results confirmed specific language, creating safe spaces, allowing permission for self-care, and engaging intergenerational role models were essential to cultivating a successful community-based ecosystems approach. Evaluation of the most effective health and healing strategies concluded that the programs with the greatest impact helped reduce stress and improve school performance.