Paying for capital transportation projects is a major challenge for many state agencies, made more complex by the passage of Dodd-Frank and the COVID-19 pandemic. This report guides practitioners through the process of debt-financing. It clearly describes the federal regulations, economics, federal institutions, and program needs that govern debt issuance and management, and it goes into great detail for each phase of the debt-financing process. The four phases are the decision process, individual transaction preparation & development, marketing & placement of individual transactions, and post-issuance compliance strategy. Three key challenges are also addressed in the guidebook: accessing complete information, planning for economic uncertainty, and adapting to technological advances.