Barriers to climate change adaptation have received increased attention in recent years as researchers and policymakers attempt to understand their complex and interdependent nature and identify strategies for overcoming them. To date however, there is a paucity of research on barriers to transformative adaptation. Using two case studies of flood risk management from Ireland we identify and characterize barriers to transformative adaptation. Qualitative semi-structured interviews were conducted with key stakeholders connected to proposed transformative strategies in Skibbereen, County Cork and Clontarf, County Dublin. Across both case studies, where transformative strategies failed to materialize, we highlight three significant barriers that impede transformation including: (i) social and cultural values, particularly place attachment and identity; (ii) institutional reliance on technical expertise which fails to look beyond traditional technocratic approaches and; (iii) institutional regulatory practices. Findings illustrate that where social or institutional barriers emerge, transformation may more likely succeed through a series of incremental changes. This research has practical implications for future adaptation planning as facilitating transformation through incrementalism requires flexible adaptation strategies that are responsive to changing social values over time. While focused on flood risk management, our findings have applicability for other sectors adapting to climate change.