Rangelands in southern Africa are degrading as human pressure on them increases. Better grazing management is clearly needed. Intensive management can also be applied to a few small areas, such as by harvesting rainwater to soak into the ground and support the growth of natural grasses and planted trees. Initial experiments were attempted at three sites by digging contour ditches, and in addition by constructing ponding banks at one of those sites. Earthmoving machinery was used at a 100 ha rural site, while contour ditches were manually dug with pick and spade at two small urban sites. Diverse tree species were planted below contour ditches for different functions and products, including ‘chop-and-drop’ mulching, tall protective canopies, and edible leaves, fruits, and pods. Much of the low rainfall experienced was soaked into the ground. However, the initial survival rates of tree seedlings was low, suggesting that tree planting should await some years to allow sufficient rainwater to be planted first. Useful lessons were learned from the various designs of infrastructure tried, which will be applied to further evolve appropriate regeneration methods. These must be integrated with other techniques that address the root causes of degradation, such as through the appropriate management of grazing and fires, while fitting into the heterogeneity occurring at different scales in the landscape.