During the Cold War, Nepal positioned itself amid the complex interplay between international and regional politics. The country experienced the impact of the two layers of Cold War politics: the first was the ideological competition between the US and the Soviet Union; the second involved regional rivalries between China and India. Internally, Nepal also struggled both politically and economically. Politically, the Cold War period witnessed multiple regime changes with varying governance styles. Economically, the poor developmental foundation and the impoverished state of physical connectivity in Nepal rendered the country an amalgam of remote and disconnected regions. Confronted with the massive need to undertake nation-building, but constrained by a lack of domestic economic resources, Nepal was compelled to seek foreign aid, not only for various development plans but also for vital infrastructure projects such as highways and airports. This chapter examines how Cold War politics affected or enhanced Nepal’s connectivity prospects. It explores how Nepal’s bilateral engagements with foreign powers and donors for infrastructure development not only led to trade-offs in sovereignty but also enabled the ruling elite to strengthen their domestic political position. Given the asymmetrical relations between donor countries and Nepal in terms of power, resources and influence, what political considerations did Nepal need to account for while accepting such bilateral investments? At what geopolitical and security costs to the country? What foreign policy interests did Nepal seek to pursue, and why? This chapter aims to find answer to these questions by studying connectivity initiatives and foreign aid politics of the four major donor countries—India, China, Soviet Union and the US. The chapter also examines how Cold War multilateralism influenced Nepal’s prioritization of connectivity projects and whether it facilitated or hindered bilateral connectivity initiatives.