This chapter discusses the 1953 legal challenge to Ceylon’s (present-day Sri Lanka) voter registration laws before the Judicial Committee of the Privy Council in London, one of the first against domestic legislation on citizenship from a former British colony. The Kodakan Pillai appeal, as the case was known, was part of multiple challenges to the immigration, nationality and citizenship regime in Ceylon at the time which discriminated against people who had migrated to Ceylon from India but had permanently settled there for multiple generations. The appeal ultimately failed, and the malaiyaha thamilar – plantation laborers and their descendants – form part of minority populations in Sri Lanka today, stigmatized as ‘migrants’ and outsiders, frequently lacking documentation and evidence of citizenship, and consequently, to land ownership or welfare benefits. Drawing on a rich legal archive of citizenship applications filed before the Commission for Indian and Pakistani Residents in the 1950s, alongside the Kodakan Pillai appeal, this chapter serves as an illustration for why the legal history of statelessness in Asia is important. Given this historical context, it also cautions against solutions to statelessness in the region that solely rely on improved documentation of political belonging.