: This paper explores the relationship between the environment and human wellbeing whilst considering water resource pressures in the context of ecosystem services, before assessing the management actions to facilitate human wellbeing under the European Union’s Water Framework Directive (WFD). By focusing on four river basins in four European countries currently working to implement the WFD, we explore the effects of multiple pressures faced within each one on human wellbeing. Under an Ecosystem Services framework, we identify those effects and consolidate them into Human Wellbeing Factors to assess the management actions. Then, by conducting a qualitative content analysis, we assess the effectiveness of each Program of Measures at river basin level and relate them to Human Wellbeing Factors. Findings indicate that factors such as population growth trends intensify the effects of these pressures on human wellbeing. Finally, the paper pinpoints that human wellbeing must remain an ever-present consideration to be weighed against any other competing policy objectives.