This chapter examines the Stalinist dual-structured model of social security, its adoption, and its fate in socialist China (1949–1978), with a focus on its generosity. It argues that this Stalinist model, formed in the 1930s, featured an urban-rural divide in its structure to provide social benefits to urban and rural residents, respectively. This model was adopted in China in the 1950s with adaptations to China’s material backwardness. Its implementation in the decades after 1956–58, however, was deeply influenced by Maoism, which departed from Stalinism. While the Stalinist model encouraged differentiation of benefits for urban and rural residents, Maoism emphasised egalitarianism to eliminate the urban-rural divide inherent in the Stalinist model through voluntarism (stressing human willpower), as expressed in mass campaigns and class struggle. But Maoism could not surpass the Stalinist framework and thus failed to abolish the urban-rural divide. The result was different fates of the differing elements of the dual structure of China’s social security under Mao: the weakening and breakdown of labour insurance contrasting with the expansion of the Cooperative Medical System (CMS) towards universal inclusiveness. The CMS ultimately provided rudimental but effective social protection to Mao’s peasants, while labour insurance was suppressed.