Re-excavation of Ha Makotoko and Ntloana Tšoana rock-shelters in western Lesotho, produced abundant faunal remains (both macro and micro) from people using the Robberg technocomplex during the late Pleistocene (Ha Makotoko and Ntloana Tšoana (15.4–13.4 kcal. BP) and early Holocene (Ntloana Tšoana 11.1–10.2 kcal. BP). This faunal material allows us to identify the subsistence strategies they employed, using the unbiased Simpson's evenness index (1-D′), and Shannon's evenness index to track diet breadth. Detailed analyses of the sites' microfauna indicates that eagle owls and/or small carnivores — not humans — were responsible for introducing them into the deposits. A chi-squared test comparing diet breadth across the sites identifies hunting strategy, focused on size 2 and 3 migratory ungulates (equids, suids, and bovids), supplemented with size 1 and 4 bovids. Comparing the evenness values from Ha Makotoko and Ntloana Tšoana to published data from other Robberg-associated sites in the wider Maloti-Drakensberg region (Sehonghong, Rose Cottage Cave and Tloutle) allows variability in subsistence strategies to be addressed. A chi-squared test comparing ungulate size classes, small mammals and fish with the evenness index reveals two important statistical differences: the warm period occupation (16.5–14.3 kcal. BP) at Rose Cottage Cave presents a narrow diet heavily focused on size 3 ungulates (with a lack of fish). At the other end of the climate spectrum, cold conditions at Sehonghong immediately before the Last Glacial Maximum were associated with a narrow diet focused on intensive fishing, with lower-than-expected numbers of size 3 ungulates. The deposits at Ntloana Tšoana, Ha Makotoko, and Tloutle, along with the Younger Dryas-associated assemblage from Sehonghong, on the other hand, present broad diets. Fish and small mammals make more of a contribution to the expanding diet in the highlands. Our approach demonstrates the flexibility that makers of Robberg tools displayed in adapting to the changing climatic and ecological conditions of this high-elevation region in the interior of southern Africa during Marine Isotope Stage 2 and across the Pleistocene/Holocene transition.