The purpose of this study was to examine middle school outreach to families about student behavior and its relationship with student school behavior, conduct problems, emotional symptoms, prosocial behavior, as well as school safety. In addition, the role of school implementation of positive behavioral interventions and supports (PBIS) was examined as a systems-level approach that could promote school outreach to families. Participants were 653 teachers and 12,912 students across 41 public middle schools in the Northwest region of the United States. The longitudinal data were examined using multilevel regression models in which repeated measures at the school level were nested within schools. Residualized change in school-level outcome was modeled as a function of current and prior measures. Findings suggested that teacher report of school proactive outreach to families predicted greater teacher report of school safety, as well as declines in student report of conduct problems and emotional symptoms. In addition, results suggested that school outreach was associated with teacher report of student school behavior. Implications for continued research on school-home communication, as well as implications for embedding proactive school-home communication approaches in school systems and practices, are discussed.