Transportation systems are vital to the U.S. economy and way of life, and major disruptions to transportation networks associated with natural hazards, man-made hazards, accidents, or infrastructure failure can cause significant social and economic impacts. Risk management tools, including insurance and mitigation measures, can reduce the impacts and recovery times associated with disruptions, but are lacking in many transportation systems. Through literature review and interviews with insurers and infrastructure managers, this study identifies barriers and opportunities to improving infrastructure resilience and develops recommendations for financial, insurance, and policy measures to facilitate improvements in transportation infrastructure resilience. Key themes identified include the need for better data and metrics to support resilience, issues surrounding emerging risks, reliance on federal disaster funding, benefits of linking risk engineering and insurance, and insurance as a tool for resilience financing. Speakers University of Pennsylvania Gina Tonn, Postdoctoral Research Fellow, Wharton Risk Center Jeff Czajkowski, Managing Director, Wharton Risk Center Howard Kunreuther, Academic Co-Director, Wharton Risk Center