The subsidiarity principle of water resources management suggests that water management and service delivery should take place at the lowest appropriate governance level. The principle is attractive for several reasons, primarily because: 1) the governance level can be reduced to reflect environmental characteristics, such as the hydrological borders of a watershed that would otherwise cross administrative boundaries; 2) decentralization promotes community and stakeholder engagement when decision-making is localized; 3) inefficiencies are reduced by eliminating reliance on central government bureaucracies and budgetary constraints; and 4) laws and institutions can be adapted to reflect localized conditions at a scale where integrated natural resources management and climate change adaptation is more focused. Accordingly, the principle of subsidiarity has been welcomed by many states committed to decentralized governance, integrated water resources management, and/or civic participation. However, applications of decentralization have not been uniform, and in some cases have produced frustrating outcomes for states and water resources. Successful decentralization strategies are heavily dependent on dedicated financial resources and human resource capacity. This article explores the nexus between the principle of subsidiarity and the enabling environment, in the hope of articulating factors likely to contribute to, or detract from, the success of decentralized water resources management. Case studies from Haiti, Rwanda, and the United States’ Florida Water Management Districts provide examples of the varied stages of decentralization.