Throughout the twentieth century, many Europeans agreed that individual freedom had to be defended against an oppressive state. Dissidents strove to do so at the risk of imprisonment and physical violence. Political radicals and neoliberals accused even democratic states of undermining the very possibility of living freely. But for others the relationship was far more equivocal. Social democrats promised to foster working-class people’s freedom by expanding the welfare state, thus rendering them independent of capitalism and the family. Even major dictatorships, out of an interest in mobilization or acquiescence, did not present themselves solely as collectivistic projects. Whether or not the power of the state promoted or stifled freedom thus remained a matter of controversy. This chapter explores three aspects of this relationship: how inmates of concentration and work camps in Stalin’s Russia, Hitler’s Germany, and Franco’s Spain were deprived of their freedom but desperately attempted to safeguard some vestiges of it; how the Third Reich, various Eastern Bloc regimes, and the late Francoist dictatorship tried to accommodate individualistic desires and demands within their repressive structures; and, finally, how the project of social democratic liberty took shape and was challenged from both the left and the right.