In this chapter we address the relationship between climate adaptation strategies and the broader institutional context. Institutions, we argue, shape policy responses to climate change. Questions in the literature have been raised whether incremental, often technocratic, adaptation strategies are sufficient to address the future risks of climate change. Instead, broader societal transitions and transformations may be required, embedded in adaptation strategies resulting from drastic, catalytic change. Transformational policy responses to climate change are apt to reshape interactions between, and within, human and natural systems. However, scaling up adaptation strategies to spur catalytic change encounters significant institutional constraints, leading to inertia. We study the adaptation literature to discern drivers that generate institutional inertia and discuss their implications for employing incremental and transformational adaptation strategies. These drivers are also discussed critically by exploring how institutional inertia can be challenged.