In 1991, just after the re-independence of Estonia, people who had held Soviet citizenship – then rendered stateless – constituted 32% of the population. In 2018, the proportion was 6%, meaning that approximately 77,000 individuals had not naturalised in 28 years. What is more, an additional 18,000 young stateless persons have been born and raised in Estonia in the same period. These people have had (and continue to have) the possibility to acquire Estonian citizenship through the naturalisation process. At the same time, they also have the option of rejecting it and living with an unidentified citizenship. Such a status sets some restrictions (such as lack of free movement within the European Union and lack of voting rights), but does not limit their everyday life to a substantial extent. The aim of this chapter is to explore the motivations of young stateless people in acquiring Estonian citizenship in the face of continued statelessness. Through secondary data analysis, combined with in-depth interviews with stateless young people, findings indicate that citizenship is not simply about a rational pursuit of state rights and benefits, but involves questions about belonging, nationalism, and legitimacy. While there are practical reasons for not acquiring citizenship, the stateless youth in Estonia have experienced overall exclusionary attitudes from the majority population and the state via national policies. Moreover, the citizenship process has proven to be so uncompromising that even people who have gone to Estonian schools, speak Estonian, and are integrated into Estonia have not always managed to naturalise.