This chapter examines how community support and network-based casework can help prevent school dropout and promote the well-being of vulnerable youth. Grounded in systems theory, empowerment, and strengths-based approaches, the chapter presents a case study from Võru County, Estonia, where the LÕIM intervention program was developed to address the complex needs of students at risk. The program brought together local municipalities, schools, social and youth services, and other stakeholders to build coordinated, cross-sectoral support systems tailored to local contexts. Drawing on qualitative data from group interviews with 34 professionals across five municipalities, the chapter explores how interdisciplinary collaboration, early risk identification, and integrated case management contributed to more inclusive and responsive educational environments. Key findings highlight the importance of trust-building, clearly defined roles, and shared responsibility among professionals, as well as the need for continuous professional development and peer support mechanisms such as supervision. The LÕIM model demonstrates how community-driven strategies—when combined with structured collaboration and targeted training—can strengthen local systems and better support children and youth facing educational challenges. This chapter contributes to global conversations on dropout prevention by offering practical insights into the role of community-based interventions and the power of systemic, locally grounded approaches.