Abstract. Water productivity in smallholder rain-fed agriculture is of key interest for 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 in situ WH and supplemental water demands (SWD) in smallholder agriculture in the Thukela River Basin, South Africa. It incorporates process dynamics governing runoff generation and crop water demands, an explicit account of the reliability of in situ WH, and uncertainty considerations. The agro-hydrological model SWAT (Soil and Water Assessment Tool) was calibrated and evaluated with the SUFI-2 algorithm against observed crop yield and discharge in the basin. The water availability was based on the generated surface runoff in smallholder areas. The SWD was derived from a scenario where crop water deficits were met from an unlimited external water source. The reliability was calculated as the percentage of years in which the water availability ≥ the SWD. It reflects the risks of failure induced by the temporal variability in these factors. The results show that the smallholder crop water productivity is low in the basin (spatiotemporal median: 0.08–0.22 kg m−3, 95% prediction uncertainty band (95PPU). Water is available for in situ WH (spatiotemporal median: 0–17 mm year−1, 95PPU) which may aid in enhancing the crop water productivity by meeting some of the SWD (spatiotemporal median: 0–113 mm year−1, 95PPU). However, the reliability of in situ WH is highly location specific and overall rather low. Of the 1850 km2 of smallholder lands, 20–28% display a reliability ≥25%, 13–16% a reliability ≥50%, and 4–5% a reliability ≥75% (95PPU). This suggests that the risk of failure of in situ WH is relatively high in many areas of the basin.