Water productivity in smallholder rain-fed agriculture is of key interest for improved food and livelihood security. A frequently advocated approach to enhance water productivity is to adopt water harvesting and conservation technologies (WH). This study estimates water availability for potential in situ WH, and supplemental water demand (SWD) in smallholder agriculture in South Africa’s Thukela River Basin (29 000 km2, mean annual precipitation 550–2000 mm yr−1). The study includes process dynamics governing runoff generation and crop water demands, quantification of prediction uncertainty, and an analysis of the reliability of in situ WH.