This paper seeks to understand the drivers and pathways of local livelihood change and the prospects for transformation towards a more sustainable future. Data are used from several studies, and a participatory social learning process, which formed part of a larger project in two sites in the Eastern Cape, South Africa. Secondary information from a wealth of related work is used to place our results within the historic context and more general trends in the country. Findings indicate that livelihoods in the rural Eastern Cape are on new trajectories. Agricultural production has declined markedly, at a time when the need for diversification of livelihoods and food security seems to be at a premium. This decline is driven by a suite of drivers that interact with, and are influenced by, other changes and stresses affecting local livelihoods. We distil out the factors, ranging from historical processes to national policies and local dynamics, that hamper peoples' motivation and ability to respond to locally identified vulnerabilities and, which, when taken together, could drive households into a trap. We end by considering the transformations required to help local people evade traps and progress towards a more promising future in a context of increasing uncertainty.