The aim of the EU Water Framework Directive (WFD) is to achieve a “good” chemical and ecological status for all waters by 2027. Currently, the Netherlands and other EU Member States are finalizing their plans for the third iteration of the WFD management cycle. In this paper, we conducted an ex ante evaluation of these plans by assessing the perceptions of regional water authorities on goal attainment and the factors that account for it. In order to gain these insights, we first reviewed literature and developed a framework of factors that stimulate or hamper the implementation of the WFD. More detailed insights into the relevance and characteristics of these factors were found by applying the framework in two in-depth case studies. A more generalizable pattern was found by translating the case study results into a survey among the regional water authorities. We found that the majority of the participating water authorities expect that 50% (or more) of their WFD objectives will be achieved in 2027. However, hampering factors such as a lack of political will or the impossibility to address key causes of the problems that were identified during earlier management cycles are still present. Since it is doubtful whether they can be addressed by regional water authorities, we conclude that it will be unlikely that ecological ambitions will be met by 2027.