The disintegration of the British Empire in Asia and the emergence of new nationstates marked a period of significant upheaval for communities whose identities and mobilities were fundamentally reconstituted by a new system of borders, citizenships, and nationalities. In this article, I seek to explore a social history of early citizenship in Singapore by examining how citizenship was understood and conceived by varied segments of society during its final years as a colony. Focusing on ethnic groups considered non-indigenous, I examine the decisions made by communities and individuals with regard to Singapore citizenship, studying the period between 1957 and 1963. During this time the meaning and significance of Singapore citizenship underwent dramatic shifts, and various forms of dual citizenship were phased out in the context of political plans for Singapore’s future. I argue that individuals’ decisions about citizenship reveal how they understood their own futures after colonialism, within the region, commonwealth, and nation. The citizensubjectivities of individuals and communities often did not align with what emerged as an official discourse of exclusive loyalty and belonging. Early experiences of citizenship were instead shaped by intersections of race, class, and complex transnational identities, as well as pragmatic assessments and emotional decision making. These did not simply mirror state-driven processes but instead represented important aspects of the complex social history of decolonization in Singapore and the early transition of its inhabitants from a colonial society to a national citizenry.