Coastal hazard risk is compounded by climate change. The promise and prospects of adaptation to escalating coastal hazard risk is fraught, even in a country like New Zealand that has laudable provisions for local authorities to be proactive in adapting to climate change. Continuing property development in some low-lying coastal areas is resulting in contestation and maladaptation. The resistance of some local authorities to do the inevitable and make long-term planning decisions in the face of amplifying risk can be linked to adaptation barriers. What can be done to overcome barriers and facilitate adaptation? Is transformation of the current mismatch between short-term planning and development aspirations, long-term societal goals, dynamic coastal processes and well-intended legislation and policy goals even possible? What can we learn from adaptation failures? In the face of compelling evidence and an enabling institutional framework, why is it that some coastal communities fail to prepare for the future? We shed light on such questions based on a long-term study of experience in New Zealand’s Coromandel Peninsula. We focus on the overarching question: Why is adaptation so challenging; and why are some coastal communities locked- into maladaptive pathways? We focus on the influence of a short-term decision-making focus of the problem of a low level of understanding and, following from this, the prioritization of protective works to combat erosion. Further, we draw attention to a major storm impact and the failure to turn this window of opportunity to a shift away from business as usual. Through the exploration of key stakeholder insights, the findings from the literature are reinforced and put into local context thus making the otherwise abstract barriers locally relevant. Matching and aligning adaptation theory with local reality can assist in advancing inquiry and policy practice to govern complex adaptation challenges.