Building Cultures of Care in schools has profound potential to support students' mental health and academic success. This is critical as students' mental and behavioral challenges are rising, and teachers report stress and burn out. To inform work in other communities, we examine the Culture of Care initiative in a tri-county region of one US state. We take a Developmental Evaluation approach, documenting the journey, including successes, challenges, adaptations, and initial outcomes over 3 years encompassing the COVID-19 pandemic. In Year 1, 12 school district administrators and partners responsible for initiative launch reflected on keys to success, early outcomes, and challenges through interviews. In Year 3, 62 educators, local administrators, and community partners who implemented the initiative participated in open-ended surveys and focus groups. Results from content analysis revealed evidence of a systems approach to integrating multiple components of trauma-informed and restorative school practices into a unified initiative to create educational cultures of care. Strengths stemmed from a regional, relationship-based approach uniting educational leaders and a team of coaches across multiple districts, coupled with tailored strategies for individual schools, and adaptability to emergent needs. Challenges included escalating student needs, difficulty learning new practices, staff turnover, stress and fatigue, variability in buy-in across schools, and challenges to community and family partnerships. Yet, participants consistently pointed to indicators of success, including transformation in staff perspectives and practices, and more positive learning environments. Further research is needed to capture students' and families' perspectives and to examine equitable educational and mental health outcomes for students.