This paper details the characterisation of four obsidian artefacts from the Mesolithic site of Livari Skiadi, one of only a handful of such pre-Neolithic sites on Crete. Elemental analysis using EDXRF sources the raw materials to Sta Nychia on Melos; in concert with other data, it can be suggested that this was the preferred Melian source for Late Pleistocene – Early Holocene populations. The Livari material represents the earliest Melian obsidian on Crete and by implication the first evidence of its inhabitants' connections to the Cycladic islands. When located within a broader review of Melian obsidian use in the Upper Palaeolithic – Mesolithic Aegean, it can be shown that the main consumers of these raw materials were island-based groups with immediate access to waterways that led to the Cyclades. It is suggested that distinctions between island and mainland toolkits (technical and raw material choices) may have been the product of seasonal, and environmental influences, rather than reflecting the products of different populations. Finally, certain datasets, including Livari, suggest the procurement of obsidian via intermediaries. These exchanges are viewed in avowedly social terms, with gift-giving a fundamental manner through which inter-group relations were created and maintained, whereby the circulation of obsidian can be viewed as one of those mechanisms through which Mesolithic Aegean cultural traditions came to be produced and reproduced.