The federal road legislation of the 1950s, which built the interstate highway system and established a trust fund for financing transportation infrastructure through fuel taxes, was the historical high-water mark of U.S. political willingness to make major investments in non-military public goods. For the past several decades, tax revenues have fallen ever more behind in their ability to maintain the country’s infrastructure, let alone support major investments for building a new cyber-physical infrastructure for the connected and highly automated mobility systems now under development. Vehicle efficiency gains and lower tax collections for AFVs will worsen the financial erosion due to the failure to keep up with inflation and growth of the existing system. How will society react to this financial conundrum even as it seeks to embrace the convenience, cost savings and safety benefits of new mobility options? Questions include how consumer response to features already being introduced will influence the path going forward; which mobility modes will be used in which locations; and the resulting impacts on how the transportation system is organized. In light of the societal and economic factors: What options will be feasible for funding transportation infrastructure? To what extent can new technologies be financed privately, through highly leveraged public-private partnerships, or by using mobility-as-a-service business models handled by the telecommunication and internet firms increasingly involved in the sector?