The paper examines the regional program Diritti a Scuola (DAS), designed to combat school dropout and educational disengagement while promoting social inclusion among students. A counterfactual analysis, based on INVALSI data, compared schools participating in DAS with non-participating institutions matched through Propensity Score Matching. The findings indicate positive effects on students’ skills, particularly in the lower grades of the education system. A qualitative analysis, drawing on interviews with school principals, teachers, and experts, supports the positive impact of the program. It shows that the program’s positive impacts on students’ motivation, inclusion, and competencies are closely linked to factors such as enhanced teacher professionalism, the adoption of innovative teaching practices, and the involvement of external experts. Overall, the evaluation highlights that the program’s multidimensional model has strengthened collaboration among schools, communities, and families, thereby helping to mitigate the risks of school dropout and the intergenerational transmission of educational disadvantage.