What was it that made Homo sapiens such a successful species and the sole remaining hominin on the landscape? What enabled us to colonize the entire world and survive in novel or extreme environments? Some researchers argue the development of a new technology, called “microliths,” was a key adaptive strategy in our success and global spread. Benefits of these small tools are argued to include more efficient conversion of raw materials into usable stone tools and the creation of innovative and diverse tools that have been linked with the use of composite tools. Composite tools combine multiple components and are often linked to the spread of mechanically assisted projectile technology and hunting weapons. The appearance and spread of microliths is suggested to be part of a global trend of technological reorganization during the late Pleistocene (~126,000-11,700 years ago). However, these associations, and even definitions of “microliths,” are problematic. Definitions tend to be contextual and oscillate between broad considerations of any intentionally produced small flake and specific manifestations of small tools, such as backed geometric pieces and segments, small bladelets, or retouched blanks. This has complicated our understanding of the development, spread, and potential benefits of what is considered a pivotal technological innovation of our species. Rather than focusing on a typological definition of microliths, we must systematically address how small tools were made. By focusing on the technological system used to produce small tools in different contexts, we can understand how each system varied and whether technological systems for small tool production were convergent solutions that were reinvented or cultural knowledge transmitted within and between groups. Here, I employ technological analysis of stone tool assemblages to understand how systems of raw material provisioning and transport influence technological organization and individual systems of small tool production during the late Pleistocene and how these change from the Middle Stone Age (MSA; ~315,000-30,000 years ago) to the Later Stone Age (LSA; ~42,000-2,000 years ago) in southern Africa. I examine decisions related to systems of provisioning, transport, and the use of composite tools and projectile technology to understand how these affected the form and systems of production of small tool technologies.In Chapter 1, I introduce the questions addressed by this research: What is a “microlith”? In what ways do lithic assemblages show intentional production of small tools? And how did people’s movement around the landscape affect lithic toolkit composition and transport? In this project, I examine two “microlithic” technocomplexes: the Howiesons Poort (HP; ~65,000-58,000 years ago) and the Robberg (~26,000-12,000 years ago). In southern Africa, Howiesons Poort is one of the earliest technocomplexes where small blades and bladelets are systematically produced and retouched into formal tools. Although these are often interpreted as some of the earliest evidence for mechanically assisted projectiles, there is still much to be understood about their production. Robberg technology, included in the “late Pleistocene microlithic” spread across southern Africa just after the Last Glacial Maximum. Focused on the production of small bladelets from distinctive cores, Robberg technology is also associated with the production of composite tools and hunting weapons. I discuss the importance of identifying deliberate choices guided by tool design compared to the end point of a reduction continuum as cores near exhaustion in small tool production and discuss challenges resulting from context-specific definitions of the term “microlith.”Chapter 2 presents data from the site of Montagu Cave, South Africa. Through technological analysis of the lithic assemblage from Horizon 6/7 of Keller’s excavations of Montagu Cave, South Africa and reconstructions of chaine operatoires, or reduction sequences, I show that Howiesons Poort core reduction methods were used on the largest and smallest cores, including on cores on flakes found within the assemblage. Our results show that small blanks were produced intentionally and not as the result of a reduction continuum or extended reduction because of transport. Small blanks at Montagu Cave were produced independently of large blanks and selection for small blanks began with raw material acquisition. Large quartzite nodules were quickly reduced in size through the use of cores on flakes and finer grained raw materials started small with the selection of small raw material nodules.Chapter 3 examines the site of Nelson Bay Cave, located on the southern coast of South Africa. I provide technological descriptions of production methods used in the Level 6, the oldest unmixed Howiesons Poort layer from Klein’s excavations of Nelson Bay Cave. The Howiesons Poort technocomplex has been central to discussions of the cultural and cognitive capabilities of modern humans and the behavioral evolution of our species during the late Pleistocene. The results provide descriptions of the reduction sequences and demonstrate three notable features. First, the lithic assemblage shows branching modes of blade production beginning with core blank selection. Second, features present in the lithic assemblage suggests large blades were intentionally fragmented to produce characteristic Howiesons Poort backed artifacts. Finally, the data suggest a focus on place provisioning and use as a residential site. When these results are considered, we establish that raw material constraints do not explain the production of small blanks and tools within the assemblage and that the observed characteristics likely reflect intentional selection for small blanks and other aspects of technological decision making.Chapter 4 examines small tool production in the Robberg technocomplex. In this study, I describe the stone artifacts from a discrete cluster of stone artifacts assigned to the Robberg technocomplex at the open-air locality of Uitspankraal 9, which is located near two major sources of toolstone in the Doring River catchment of Western Cape, South Africa. Comparison of near-source artifact reduction at Uitspankraal 9 with data from three rock shelter assemblages within the Doring watershed – Putslaagte 8, Klipfonteinrand Rock Shelter, and Mertenhof Rock Shelter – suggests that “gearing-up” with cores and blanks occurred along the river in anticipation of transport into the wider catchment area. The results reveal an integrated system of technological supply in which raw materials from different sources were acquired, reduced, and transported in different ways throughout the Doring River region.In Chapter 5, I present the first descriptions of lithic assemblages assigned to the Robberg technocomplex from the site of Knysna Eastern Heads Cave 1 (KEH-1), located on the modern-day southern coast of South Africa. During the Last Glacial Maximum (~20,000 years ago), the landscape off the southern coast was a different world than it is today. At its most extreme, the modern-day coastline was up to 75 km from its present position. Technological organization at KEH-1 differs in key ways from other published Robberg assemblages, showing lower reduction intensity, infrequent use of bipolar percussion, and low emphasis on lithic miniaturization. Our results suggest that site dynamics at KEH-1 differ from other sites and may represent a logistical resource extraction camp targeted at lithic raw material acquisition. Data from KEH-1 highlights the importance of understanding how resource distribution and site dynamics influence lithic technological organization.Chapter 6 provides concluding remarks and directions for future research.