Water rights involve an amalgam of property rights and socio-economic rights that possess an inescapable regulatory dimension. The resulting uneasy mix of public responsibilities and private property regimes means that the details of the legal entity structure involved are central to the viability and effectiveness of implementing water rights on the ground. Small-scale social enterprise structures offer a fascinating site for exploring the tensions endemic to the field of water rights. This article explores the ways in which the entrepreneurial energies of business approaches to the implementation of water rights articulate with the impetus for structural change embedded in practices of social activism. Our main purpose is to interrogate too easy an assumption of uni-dimensional or static relationships between social activism and social enterprise. We argue that there are multiple diverse relationships possible between them, including oppositional, evolutionary, complementary, and dialectical relations. We illustrate these shifts empirically with examples from India and Bolivia. The article stresses the ambiguous potential of both empowerment and oppression when business methods are used to secure social outcomes, including those promised by the guarantee of a human right to water.