Schools have an increased focus on implementing schoolwide initiatives (e.g., multi-tiered systems of support; MTSS) to address risk factors related to dropping out. These interventions can involve multiple domains, including academic, behavioural, and social and emotional supports. Although researchers suggest that schoolwide interventions are effective, school staff may need help implementing various content (e.g., academic, behaviour) domains into a cohesive plan. This preliminary study focused on nine schools in the Midwestern United States that implemented schoolwide interventions as part of a statewide technical assistance approach. The research included using survey and extant data for all students to determine the connections between schoolwide interventions, school improvement, and student outcomes. Schools in this study that were higher on both school improvement and MTSS implementation had, in general, better student outcomes associated with predictors of dropping out of school. These findings indicate that school improvement and MTSS may be mutually beneficial enterprises that help school staff address factors related to dropping out.