Approximately 20% of youth in the U.S. are experiencing a mental health challenge; a rate that is said to increase by more than 50% by 2020. Schools are the largest provider of mental health services to youth, yet two of schools’ most efficacious evidence-based systems, Positive Behavioral Interventions and Supports (PBIS) and school mental health (SMH), often exist in isolation. Interconnected Systems Framework (ISF) unites these two systems to improve school and life outcomes for all students, but especially, students who struggle with or are at risk of developing mental health challenges. The current study measured New York City metropolitan area principals’ initial readiness to implement ISF. This researcher found that principals in schools that implemented PBIS indicated significantly greater levels of initial readiness to implement ISF than principals in schools that did not implement PBIS. Sequential multiple regression models showed the variance of independent variables, elements of ISF, that predicted initial readiness to implement ISF. The elements “teaching appropriate behaviors to all students” and “acknowledging all students for behavioral achievement, school-wide”, serve as strong recommendations for principals in the exploration and adoption stage of ISF. As policy makers prepare for the new presidency and the inception of the Every Student Succeeds Act (ESSA), they should reflect on the goals, strengths, and needs of their students and equip students, families, schools, and communities so they can be achieved. Although most of data analysis yields to no significance, that in and of itself is significant. Student need and implementation challenges are consistent across the region.