This article uncovers the Scottish Highlands’ earliest-known overseas slave-owning circle and the imperial entanglement with the Dutch Empire and its sugar on which this depended. It thus provides a case study of the transnational, Dutch-influenced nature of commerce in a non-metropolitan part of northern Europe in the later seventeenth century. The article highlights two interconnected contemporary developments: the engagement of Highland migrants or exiles in the sugar-based enslavement of African and indigenous populations in Suriname; the region’s heavy reliance on the importation of sugar with origins in the Dutch Atlantic plantations. In this way, the article illuminates both north Highland agency in the oppressions of the ‘triangular trade’, and its merchant community’s opting for Dutch over Lowland Scottish-refined sugar when supplying and encouraging local demand at that time. Taken together, this demonstrates the early enmeshment of the region in transnational ‘circuits’ of slave-owning and the interconnected seepage of sugar across broader sections of the northern European economy than previously considered. A Scottish Highland-led circle is shown to have grown prior to the formal creation of the British Empire, simultaneous with the commercial activity of Dutch Suriname-based sugar planter, Henry MacKintosh, who developed strong ties linking the colony with New England, Rotterdam, and his home burgh of Inverness.