Flooding is creating growing losses for communities, infrastructure, agriculture, and insurers, while natural infrastructure—wetlands, floodplains, working-land practices, reforestation, and green stormwater systems—offers the potential to reduce risk while delivering water-quality, habitat, carbon, and community benefits. But moving from promising projects to implementation at watershed scale requires more than demonstrating environmental value. It requires clarity around who benefits, who pays, who bears risk, what evidence decision-makers need, and how public funding, private capital, insurance, environmental markets, and catalytic investment can work together. This invitation-only working roundtable will bring together leaders from insurance and reinsurance, banking and blended finance, public finance, conservation delivery, philanthropy, resilience modeling, and environmental markets. Drawing on a recent Mississippi River Basin feasibility effort led by Ducks Unlimited with Munich Re and research partners, participants will explore two contrasting watershed pilot settings and focus on a practical question: What would it take to make watershed-scale natural infrastructure a financeable resilience asset—and move from a promising project to a transaction? The session is designed as a candid working discussion rather than a formal panel, with the goal of identifying evidence requirements, counterparties, financing gaps, and actionable next steps for pilot implementation.