Over the past two decades the discourse on social enterprise has emerged as a powerful intervention for addressing socio-economic deprivation in communities across the globe. Although the concept is increasingly attracting academic interest, there are still several areas requiring further scrutiny. One such key area is how the legal structures of social enterprises influence their outcomes. Drawing on a qualitative case study approach in South Yorkshire UK, this study contributes to ongoing debate on social enterprise by providing insights into the nature of legal structures and related operational issues across the region. The findings revealed that type of legal structure is intricately linked to social enterprises’ ability to achieve their objectives. Rather than rely on traditional legal structures, social enterprises in South Yorkshire have adopted innovative legal vehicles that help them to achieve financial sustainability while at the same time maintaining their social ethos.