The study explores the diverse landscape and ecosystem that have developed since the first known social enterprises appeared in Singapore almost 90 years ago. The buzz around social enterprises in Singapore is growing louder and more insistent. By 2013, there was, on average, one article every two days that used the term. Yet, one does not have to scratch too far beneath the surface of this energy and enthusiasm to realize that there is little consensus on what the primary characteristics of a social enterprise should be. While it is fair that a rigid definition could circumscribe the evolution of a business form that is based on the changing needs of a community, the continued growth of the sector is arguably stymied without some general agreement on its primary characteristics. In that regard, the study sheds light on the core principles defining a social enterprise and presents the challenges and opportunities facing this disctinct sector in Singapore.