This paper examines the history of St. Louis, Missouri in coping with flood risk over the past 15 years, with a focus on flood insurance. Six challenges to the continued management of riverine flood risk are identified and discussed. They are (1) many property owners don’t buy flood insurance, (2) people underestimate flood risk, (3) we need better flood maps, (4) we have a “love affair” with levees, (5) flood risk is increasing over time, and (6) we take deep pride in rebuilding after a disaster. Recommendations for how to improve flood risk management in light of these challenges are offered. Focused attention is given to the possibility of long-term flood insurance contracts tied to long-term loans for risk-mitigatingactivities in overcoming the six challenges.