Archaeological explorations of the meaning of ‘trade objects’, such as glass beads and cowrie shells, remain hampered by theoretical and methodological limitations in both their analyses and interpretations. In this paper, we develop a methodology for critically engaging in multi-scalar questions of the circulation, exchange, and value of cowrie shells in African archaeological contexts. Species, size, dorsal modifications, and depositional contexts were compared across five sites from South Africa dating between 750 and 1350 CE. These results were positioned within a review of cowries from archaeological sites in the region and compared to the documented distribution of cowries from wider African archaeological contexts. Monetaria annulus were the prevalent cowrie species in southern African archaeological contexts over the last 2000 years, with a notable absence of Monetaria moneta, prevalent at contemporaneous sites in West Africa, as well as a variety of endemic southern African species. Breakage patterns on the dorsal surface correspond to different modification techniques, such as chipping and grinding. Combined analyses of modification, use-wear, and depositional patterns show variation, revealing a diversity in the biographies of individual cowries. While a comparison of the distribution of cowries across the continent confirms the circulation of cowries through known trade routes, such as the trans-Saharan trade network and the European mercantile network, they also reveal new pathways for exchange that highlight the need for further exploration of intra African networks. Finally, the breadth of the results of this study demonstrates the value of a focus on a specific artefact to address a wide range of themes, from exchange to the archaeology of everyday life.