The end of apartheid created great expectations for the majority of South Africans in terms of political, but also social and economic change. At first glance, significant progress has undoubtedly taken place, beginning with the adoption of a very progressive Constitution and legislation protecting civil, economic and social rights. However, 15 years into democracy, after a fourth free general election, many feel that their expectations have not been met and their frustration is turning violent, as demonstrated by several large-scale strikes since 2006. Politically, this frustration has led to a blunt repudiation of the country’s leadership during the ANC conference of December 2007 and to Mr. Zuma’s ANC unambiguous victory during the 2009 general elections, despite the formation of a breakaway party. This article explores these frustrations through the evolutions that have taken place in the workplace – a central locus of exploitation under apartheid – since the late 1980s; it highlights the necessity of an analysis that goes beyond the sole prism of labour market legislation. Drawing on extensive empirical research, it focuses on the evolution of working conditions in three key sectors of the South African economy – mining, forestry and agriculture. It argues that the post-apartheid era has witnessed a marked increase in the precariousness of workers’ status and situations. Despite formal labour market regulation, processes of externalisation have been pervasive, turning previously oppressed wage labourers into poor, casualised workers eking a living in a liberalised economy. South Africa’s social and economic policies have decisively contributed to this outcome. The paradox is all the more significant when it is pitted against the high expectations associated with the transition; it epitomises the difficult restructuring of South African society and the uncertainty surrounding its future.