Mental health needs among children in the United States have significant consequences for children and their families, as well as the schools that serve them. This qualitative study evaluated the second year of an innovative school-based mental health project that created a multi-system partnership between an urban school district, a public mental health agency, and a local university to better meet the mental health needs of youth. Through in-depth interviews with seven principals and assistant principals at the project schools, four major themes were identified: (1) connecting the dots, (2) strengths and successes, (3) project significance to school and community, and (4) challenges and future directions. Findings from this study may be useful to other schools and communities who are considering school-based interventions to support at-risk youth.