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This article provides an overview of federal transportation funding, specifically how the country is failing to invest in its infrastructure. Many of the most critical systems are aging, deteriorating, and severely congested which is crippling the country’s economic development. It portrays the road ahead as very challenging because the United States is still facing substantial fiscal challenges, including budget deficits and massive debt. Goes on to provide a historical overview of federal financing for transportation, how it differs from state governments, the difficulties in securing transportation funds, and the dire need to improve these models, including suggestions on how this can be accomplished.