In disadvantaged educational contexts, students often rely on teachers as their primary providers of emotional and developmental support, especially when familial structures are unstable or absent. However, teachers themselves—tasked with delivering care, guidance, and academic instruction—face elevated stress and burnout, which undermines their capacity to serve effectively. This deterioration in the user–provider relationship contributes to a breakdown in trust, motivation, and engagement, increasing the risk of school dropout. We propose and evaluate an intervention that strengthens this relationship by offering psychological support and structured peer dialogue to teachers in 54 middle schools in Campania, Italy. Through a randomized control trial, we assess how enhancing providers’ wellbeing and relational capacity affects users’ educational outcomes and aspirations. By reframing dropout prevention through the lens of relational service delivery, this study offers novel insights into how provider support can transform user trajectories in fragile systems.