The implementation of the Water Framework Directive (WFD) has represented a unique opportunity to enhance the regulatory capacity of public agencies and restore the ecological condition of water bodies in the European Union. This paper examines the experience of translating the new Directive into practical policy-making in the Douro River Catchment in the north of Portugal. Regional development and the evolution of water management are initially described, which then inform the assessment of the achievements and failures of the new regulatory regime. The higher level of concern for environmental impacts and the integration of responses that follow the WFD can be identified as positive steps in the direction of resolving lasting water management problems. However, the translation of the Directive into national legislation has also reinforced techno-bureaucratic practices and politico-economic centralisation, as well as led to various forms of contestation and protest. It is suggested that two main reasons account for those difficulties: the sociospatial rigidity (i.e. the fragmented and static understanding of ecological and social interactions) and the monotonic categorisation of water management issues (i.e. upfront decisions with limited scope for innovation and creativity at the local level). Overall, the success of the WFD seems to depend fundamentally on the ability to perceive the broader socionatural complexity of water management and on the pursuit of more effective forms of negotiation and social inclusion.