Humans occupy a wide range of environments, including those that experience water stress. Our species has a long history of mitigating arid and semi-arid environmental risk through cultural and technological behaviors. Identifying Pleistocene foraging behaviors in water-stressed environments is particularly instructive for understanding the development of behavioral plasticity and the dispersal of modern humans. However, evidence for adaptability can be difficult to ascertain from archaeological deposits in marginal environments where occupation intensity may be light. In this study, landscape decision-making is inferred from expectations derived from the “whole assemblage behavioral indicator” approach to the formation of lithic assemblages. This model is tested against surface artifact density data from the Southern Kalahari to identify landscape provisioning structure in semi-arid environments. Our results indicate place provisioning strategies including logistic foraging, with evidence for increased occupation duration in areas closer to water. This pattern is contrasted with the published record at White Paintings Rockshelter in the Middle Kalahari, where a collector strategy is inferred. Variable means of achieving water security may have been key underlying behaviors for the dispersal of our species into marginal environments, and this study provides baseline evidence for some of the flexible land-use strategies used in the Kalahari Basin.