This chapter discusses normative aspects of Conditional Cash Transfers (CCTs) and arguments for unconditional cash transfers such as Universal Basic Income (UBI) projects. It begins by examining an institutional experience from Brazil in the first decades of the twenty-first century, the “Programa Bolsa Família”, to discuss three issues. The first is the theoretical foundations of conditional and unconditional cash transfers, mainly related to the expected effects of challenging poverty and promoting social citizenship. Secondly, the chapter discusses the ideas of autonomy, social security, and citizenship as aspects of social welfare. Thirdly, it associates the normative aspects of the theory of citizenship with the political economies of welfare-states. The chapter is based upon historical and political literature about the Brazilian case but its central argument is developed through interpretations of works of Thomas H. Marshall, Brazilian sociologist Josué Pereira da Silva, and in conclusion Gøsta Esping-Andersen. From the latter, the chapter borrows the expression “the theoretical substance of welfare-states”, which is used to present how social security policies, particularly cash transfers, relate to the realization of underlying principles of citizenship, such as equal status and social dignity.