Recently, wrap-around services have been proposed in New York as a strategy for improving educational outcomes for students. These services address non-academic barriers to learning, including housing insecurity, mental health, and lack of access to healthcare for both K-12 and postsecondary institutions. While some K–12 and postsecondary interventions have demonstrated measurable success, challenges remain in terms of implementation, scalability, and sustainability. This paper examined the impact of wrap-around services on student success to evaluate whether SUNY and CUNY Reconnect could improve student outcomes. The findings show that wrap-around supports must be paired with high-quality instruction and structural reform to yield long-term academic gains. Without structural alignment, wrap-around strategies risk falling short of their equity goals and could become a financial burden without significant gains.