Covering Marine Isotope Stages 3−2, this chapter tackles three main issues. First, it explores how hunter-gatherer societies across southern Africa coped with the challenges and opportunities of living in the highly variable ecological conditions that marked this period. Not just a matter of subsistence and diet, this is also a question of social interactions, knowledge, and how people related to the world around them. Crucially, the choices made operated in environments that may have been very different from those for which we have ethnographic accounts, demanding that we expand our interpretative frameworks beyond these. Second, Chapter 6 asks why the ‘cultural florescence’ of the Still Bay/Howiesons Poort is so starkly absent from almost the entirety of the material record across southern Africa between 59,000 and 12,000 years ago. Finally, it explores reasons for the profound change in stone-working traditions captured by the distinction between Middle Stone Age and microlithic Later Stone Age technologies. New fieldwork from throughout the region informs all these questions.