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Although the Middle Stone Age (MSA) of southern Africa, associated with major cultural innovation including aspects of symbolic behavior and the development of complex hunting tools, has been the focus of intensive research, well-documented contexts for the early Middle Stone Age (EMSA) are rare. Here, we present archeological and ecological data on the EMSA occupation of Wonderwerk Cave excavated by Peter Beaumont, along with the results of luminescence dating of associated sediments to ca. 240–150 kyr, overlapping with the timing of the first known modern humans. The lithic assemblage shows a shift to prepared core flake production but lacks complex hunting equipment characteristic of the later MSA. Although ocher is present, there is no evidence of ornaments or incised objects. Multiproxy paleoclimate data from Wonderwerk Cave demonstrate that the EMSA occupation occurred under significantly wetter environmental conditions than the current semiarid regime. The Wonderwerk Cave EMSA provides strong support for the argument that critical aspects of the MSA archeological record developed long after the first appearance of modern humans.