Many of the world’s coastlines are vulnerable to erosion and at risk from tidal flooding. Addressing and managing these risks presents major challenges especially when seeking to sustainably balance the requirements for coastal protection with other economic, environmental, and societal objectives. The nature and scale of these challenges varies greatly from site to site and can often be magnified on dynamic shorelines that are subject to a high degree of physical and ecological change. Applying an ongoing process of adaptive management is widely agreed to be a key mechanism for dealing with such dynamic conditions and issues of uncertainty. However, under this process it can be difficult for different stakeholders to reach a consensus about the most suitable intervention actions. In part, this can arise because there is an incomplete understanding about past, present, and, especially, future environmental processes. It can also occur due to differences in the perceptions and priorities of the relevant stakeholders. This paper reviews some of these complexities using, as a case study, recent developments of a shingle spit and tidal inlet at Pagham Harbour, on the south coast of the UK. This example provides lessons in the application of adaptive management and working with nature concepts in a particularly complex coastal setting. This paper considers these lessons in the context of the site’s history, the legal and policy framework, and established understanding about the natural environment.