This chapter explores the structural, regulatory, and geographic barriers that make infrastructure development in Hawai‘i disproportionately slow and costly, resulting in delays that reverberate across the economy and constrain growth, equity, and resilience. The analysis begins with Hawai‘i’s “geographic premium,” a persistent cost burden tied to its isolation and dependence on maritime imports, and examines the compounded impacts of the Jones Act, fragile logistics, and misaligned cost baselines. It then delves into the regulatory bottlenecks that stifle timely development, including fragmented permitting processes, agency silos, community opposition, and technological deficits. Housing serves as a case study, illustrating how overlapping regulations, inflated construction costs, and NIMBYism converge to exacerbate the state’s housing crisis. This chapter also investigates how modern approaches such as public procurement reform, design-build delivery, and transit-oriented development can foster smarter, faster, and more inclusive infrastructure. It calls for bold institutional innovations: one-stop permitting centers, digital governance, participatory planning, and regulatory sandboxes. Climate-ready and digitally inclusive infrastructure emerge as essential to economic sustainability and social cohesion. Ultimately, this chapter reframes Hawai‘i’s infrastructure challenges not as immovable obstacles but as opportunities to reimagine development through equity, resilience, and innovation. It concludes with a warning: the cost of inaction is far greater than the cost of change.