In brief, the paper firstly summarises old and new theoretical and technical issues on measuring poverty, secondly analyses poverty from different perspectives and highlights various research findings on poverty trends in South Africa and thirdly clarifies the notion of ‘second economy’ and attempts to ‘measure’ it. The analysis, as tentative as it is at this stage, demonstrates why there is an ongoing debate in South Africa about poverty and ‘second economy’. Clearly, the extent and the magnitude of the challenge that South Africa, like many developing countries, is grappling with are vast. As a way forward, a more rigorous analysis of poverty and ‘second economy’, drawing from the methodology used in the paper, could be pursued further. This would hopefully assist the dialogue about poverty and ‘second economy’ in South Africa. More importantly, policy and programmatic responses to poverty and ‘second economy’ could benefit from a systemic enquiry on relevant dynamics.