Historically, students attending school in rural and regional New South Wales have experienced poorer outcomes than their peers attending metropolitan schools. The lack of coordinated support services for students with complex support needs compounds this issue. Wraparound models of support have been successful in improving outcomes for students with complex support needs, and the New South Wales government has prioritised the establishment of strong relationships between schools and communities to overcome the limitations of geographic isolation. The aim of the current study was to explore wraparound support for students with complex support needs attending schools in rural and regional New South Wales. A qualitative research approach was employed, and semi-structured interviews were conducted with key stakeholders to gain an in-depth understanding of current successes, barriers, and needs. The findings indicated that wraparound was most effective in rural and remote schools when school staff implemented bespoke approaches to wraparound, such as restorative practices. Resourcing was a barrier found to be central to all schools. Recommendations are provided to enhance the capacity of rural and regional NSW schools to provide wraparound support for students with complex support needs.