Risk insurance mechanisms have been proposed as proactive policy options to enhance the resilience of communities for coping with extreme events. Many risk insurance mechanisms require designation of “risk zones” to legalize governmental interventions. After a three-day workshop and ensuing interviews, “wicked” challenges were identified in the designation of risk zones: risk thresholds; land value; damage-reduction; land-use planning; forecast uncertainty; map accuracy; modifiable-areal-unit problem; winners and losers; single versus multiple hazards; and cross-jurisdictional administrative boundaries. A total of 56 peer-reviewed studies are synthesized that evaluate these “wicked” challenges in flood insurance programs and derive deliberative heuristics for designating risk zones in publicly sponsored insurance mechanisms.