Insurance and compensation are cited as critical elements of resilience to natural and non-natural hazards alike. As a strategy of risk management, it emphasises peace of mind, financial recompense and the swift restoration of a ‘business as usual’ status for civil, social and commercial life. Yet despite the contribution of insurance to risk management, the synergies with progressive or adaptive articulations of resilience are not sufficiently explicated. This paper explores the fundamental contradictions of insurance as a form of resilience through a study of flood risk management. It demonstrates how insurance regimes serve to structurally embed risky behaviour and inhibit change after detrimental events. As such, transformative interpretations of resilience conflict with the long-standing principles and operational norms of insurance that privilege normality. The paper concludes that, despite its currency within resilience discourses, insurance is maladaptive and that insurance regimes reinforce exposure and vulnerability through underwriting a return to the ‘status-quo’ rather than enabling adaptive behaviour.