The global distribution of modern humans is unparalleled amongst other terrestrial fauna and explaining how we have become so uniquely successful is a topic of major debate in palaeoanthropology. Examining how past populations engaged and adapted to new ecologies, rather than just when and where they first appear in the fossil record, can best be rooted in broader studies of biogeography that explicitly recognize key thresholds between major ecozones. In this paper, focus is placed on the Thar Desert, marking the boundary between the Saharo-Arabian desert belt to the west and the monsoonal Oriental zone to the east as an example of such a boundary. The goal of this study is to provide a broad synthesis of available evidence from the region, aiming to clearly communicate the nature of the existing Palaeolithic record and to identify tension and contradiction within it as foci for future research. Following review of modern ecology and palaeoenvironmental archives from the region, a quantitative analysis of the Palaeolithic record of the Thar Desert is presented. Hierarchical clustering is used to evaluate the extent to which typological constellations within stone tool assemblages reflect the top level terminology used to group Palaeolithic behaviour, revealing six broad clusters of assemblages and three clusters of artefact types. A more detailed appraisal of dated and stratified assemblages highlights rare patterns of exclusion between Acheulean, Middle Palaeolithic and Late Palaeolithic assemblages alongside more prominent proportional differences in assemblage composition. These results are discussed in the broader context of key behavioural changes in Palaeolithic South Asia and the expansion of modern humans.