The global distribution of power is gradually shifting away from Europe to Asia and consistent changes between state actors within the region are also taking place. States such as the US, China, India, and Pakistan seem to make the strategic environment of this region more dynamic, complex, and somewhat unpredictable. The strategic quadrilateral relationship, described here as a growing systemic security dilemma, amongst these states is fairly complicated, and provides them with the incentive to play out various combinations of strategies based on cooperation, competition, and containment that, in turn, may raise the possibility of conflict between them. Also, the evolving technologies and force modernization of these four states suggests significant challenges to the strategic stability of the broader Southern Asian region. Given the anarchic nature of the security dilemma, this chapter builds the debate about how the systemic interaction of these states, their force structure, military modernizations, and future advancements lead towards shaping the regional order and security environment of the broader Southern Asian region. The chapter determines that the shifting distribution of power and competitive balancing of the power system lead to create a systemic security dilemma amongst these states based on possibilities for miscalculations and the problems of arms-racing.