This paper advances scholarly debate on the contradictions of environmental risk management measures by analyzing the determinants of flood insurance coverage among a sample of 403 residents in New Orleans, a city undergoing rapid transformation due to post-Katrina rebuilding efforts and anthropogenic modifications of climate, hydrology, and ecology. The paper focuses on several predictors including subjective flood risk perception, trust in government officials, sociodemographic characteristics, and experience with flood damage. Using binary logistic regression, the results show that the likelihood of having flood insurance coverage is associated with past flood damage and socioeconomic status. Older people (over age 65) are more likely to have flood insurance than younger residents. Race, gender, trust, and perceived flood risk are not statistically significant predictors of flood insurance. We connect our findings to the paradoxes and conflictual dynamics of flood insurance, a major risk mitigation measure. As we point out, in flood-prone cities like New Orleans, flood insurance operates as a double whammy: uninsured or underinsured homes face pervasive risk of both flooding and rising insurance premiums under the conditions of global climate change.