Examining the variability of enslaved life across the Atlantic World during the seventeenth, eighteenth, and nineteenth centuries is increasingly possible with the availability of comparable data. This project explores the complex networks that slaves developed between the fields of the plantation and spaces beyond its borders. Throughout the eighteenth and early nineteenth centuries, enslaved people living and working on sugar estates across the Caribbean cultivated their own subsistence food crops. In Jamaica, planters implemented this cost-cutting system of self-provisioning in areas unsuitable for sugar cane agriculture. A comparative, quantitative approach elucidates the conditions that facilitated enslaved people's cultivation of surplus in these areas and their access to markets that fostered Jamaica's internal market economy. To systematically examine surplus and access, this project integrates documentary and archaeological sources germane to provision ground suitability and the acquisition of costly market goods. GIS (Geographic Information Systems) analysis of cartographic data drawn from historic survey maps of sugar estates defines the areas available for provision cultivation. Assemblages recovered from slave village contexts on four estates provide a broad sample of goods that enslaved people acquired in the market. The results suggest that the hypothesis that enslaved people with access to a larger amount of provision grounds with favorable conditions had greater access to the markets holds for this dataset. While the areas for surplus production were poor relative to the cane fields, variation between estates in conditions and observable artifact attributes indicate the investment in ceramic vessels based on cost. More broadly, the evidence demonstrates the connections that enslaved people established to turn an exploitative system to their advantage.