The global infrastructure gap has continually widened over the last few decades. Industry reports and academic publications suggest that, in terms of road infrastructure, both advanced and developing economies have not paid sufficient attention to modernize their infrastructure assets. A wider road infrastructure gap signifies that highway conditions have declined because governments have not had enough resources for maintenance and rehabilitation. In the same way, it also indicates that congestion levels have grown and the level of service in most road networks has dropped because public agencies have not had sufficient funds to generate new highways and expand existing corridors. This dissertation, therefore, provided insights into the difficulties associated with improving the existing highway assets and the barriers related to expanding the current roadway capacity through public-private partnerships (PPPs). The research involved three interdependent studies. In the first study, I examined the continuous deterioration of the US highway system through a system dynamics model, which focused on the dynamics of capital investments and maintenance expenditures in the US road infrastructure. The results confirmed that the American highway system is currently stuck in a capability trap. This makes it difficult for the system to improve at the rates required by the country's economic growth. In my second investigation, my attention shifted toward the governance challenges related to building new roads and expanding highway capacity through PPPs. I developed a systems map of governance variables informed by past-published evidence from actual projects. By specifically examining the shaping phase of public-private initiatives, the work uncovered the effects of feedback relationships and interdependencies on PPP feasibility. This offered insights about the relationship between governance mechanisms and successful PPP development. In the third study, I utilized variables and relationships identified in my second investigation to develop a management flight simulator in order to better explain governance difficulties in the procurement phase of PPP projects. The simulator was implemented during an educational exercise with graduate students of civil engineering. By doing so, I confirmed that the simulator has the potential to increase our understanding of PPP procurement processes. Results indicated that the simulation tool was a suitable instrument to explain how government capacity, project uncertainty, and technical complexity influence PPP tendering. Overall, my findings across the three studies illustrate different means to understand why closing the global road infrastructure gap is challenging. Together, the three inquiries indicate that examining the road infrastructure sector as a socio-technical system contributes to improve our understanding of the expenditure dynamics related to existing assets and to enhance our comprehension of the governance challenges associated with developing new roads. / Ph. D.