This paper explores changing development and infrastructure projects, as well as the people’s understandings of them, at the end of the twentieth and beginning of the twenty-first centuries in the Sultanate of Oman. With the 1970 coup d’état that brought Sultan Qaboos bin Said al-Bu Saidi to power, Oman began to witness highly dramatic transformations. Within ten years, roads, hospitals, and schools among many other changes, altered the infrastructural and social landscape of the country. The drive for development has continued, functioning in many ways as what James Ferguson once called an “anti-politics machine.” This paper asks, however: What happens to people’s sense of “change” and “development” after 45 years of intensive infrastructural work that served not only to “modernize” Oman, but to shape a sense of national pride and regime loyalty? How might “development” be changing when it has served for so long as the underlying logic of state legitimacy? This paper attends to the intense focus in Oman on road building as it provides a continuation of the logic of development, while also serving national pride in engineering and a highly visible form of national connectivity. Highways along the coast, highways into the rugged and difficult mountain terrain, and, now, highways across the desert to Saudi Arabia that will require constant sand removal have become visible and glorified projects. At the same time, this paper also argues, after 45 years of development work, the threat and instances of what can be called “development fatigue” are palpable. The language of progress and infrastructural improvement may also have its political limits, not only because they fail or expectations are not fulfilled, but because they become so taken-for-granted and constant that they lose their aura. In their place, cynicism, disregard, and even boredom may prevail, even if people also recognize that failure in infrastructure or a halt to development would hardly go unnoticed.