Growing evidence suggests that adaptation will form a key component of successfully responding to climate change risks. Discussions surrounding adaptation have, until recently, placed emphasis on incremental change as a means of dealing with climate risks. However, increased attention is now being paid to transformative adaptation given the current scale of climate change impacts. Owing to its recent introduction into adaptation discussions however, little is known about the challenges associated with attempting transformative change. This thesis addresses this shortcoming. Specifically, it examines i) how and why barriers to transformative adaptation emerge; ii) how place disruption, place attachment and perceptions of governance processes are understood in response to transformative change and; iii) how incremental adaptation proceeds when transformation fails, using two case study locations of flood risk management in Ireland as examples of adaptation in practice (Clontarf, County Dublin and Skibbereen, County Cork). Employing in-depth qualitative and quantitative research methods, this thesis finds that i) barriers to transformative adaptation do not differ from those associated with incremental adaptation; ii) place attachment is strongest in individuals who perceive governance processes as inadequate, and neither flood experience nor flood risk affect strength of place attachment, support for flood defences or perceptions of governance processes, and; iii) even relatively modest incremental adaptation measures can prove extremely contentious and difficult to implement where transformation fails, particularly when past learnings are not embedded into governance practices. The findings have important implications for adaptation policy and planning. First, climate change threatens both tangible and intangible assets. Whilst current adaptation policies account for tangible assets in assessing the merits of adaptation strategies (e.g. economic damages from flooding), there exists a prevailing need to also explicitly consider intangible assets (e.g. cultural values). Second, knowledge co-production is likely to prove crucial as single actors rarely possess the knowledge, resources or legitimacy to address complex global environmental challenges. And finally, there is substantial merit in integrating virtual technologies to enhance information management between stakeholders in adaptation planning, helping to assist in eliciting emotional responses from individuals and making an abstract concept like climate change locally relevant. Moreover, they highlight the need for broad societal transformations to mitigate future climate change, helping to reduce risk and the need for adaptation in the first instance. The findings emphasize the interconnected and compounding nature of many barriers associated with both incremental and transformative adaptation, and some of the primary issues which decision-makers and communities are likely to have to contend with unless fundamental changes are made to both societal and governance practices concerning climate change and adaptation planning.