The world recently experienced the food and financial crisis. The food crisis was an indicator of the challenges towards sufficiently feeding an increasing world population. Food production through rainfed and irrigated agriculture account for the bulk of the freshwater used globally but the water is still sufficient to meet the MDG goal on hunger reduction. Agricultural water management is thus an important challenge for feeding humanity; creates the need to find sustainable methods of managing water that will include all water users. Some of these methods include rainwater harvesting which has great potential in increasing food production as compared to irrigation. This paper aims to identify challenges and opportunities for small scale rainwater harvesting in enhancing food and livelihoods security. Given the large array of practices that are classified as rainwater harvesting, infield rainwater harvesting (IRWH) developed and mainly practised in the Free State Province, South Africa is used. The technique has been in use in villages around Thaba Nchu for a couple of years. Previous studies have shown that the technique increased yield significantly, reduced risk and thus improved household food security. The paper traces the evolution of the technique based of previous studies and recent data, to identify the potential and challenges faced by adopting households. It is concluded that IRWH has great potential to improve household food security as well as contribute to sustainable rural livelihoods mainly as it can reduce dependence on market sourced food supplies.