The paper explores the inter and intra firm dynamics that are instrumental in shaping the determination of skills training within the South African labour market. The essential starting point is to show that the size of the enterprise and nature of the economic sector in which these enterprises operate, sets conditions on the regimes of enterprise training and skills development. While contesting the notion that there is inevitability in the outcome of these processes, the paper compels us to explore the reasons for it taking place in the present South African milieu. And this enables us to analyse the dynamic evolution of contractual obligations that are built on insecure and temporal employment relations. Consequently, the detour via the structural and organisation dynamics that are embedded within firms enables us to recognise the important role which training can command in promoting greater efficiencies within South African firms and halting the deleterious effects of insecurity and low productivity. The analysis leads us to the conclusion that training ultimately makes good business sense and more so if these sentiments are demonstrated and transmitted through active public policy.