As scholars have long shown, provision grounds and dooryard gardens were crucial to enslaved people’s survival and economic lives in many slave societies in the greater Caribbean. This article draws on both old and new evidence to explore the British colony of Trinidad’s late-slavery provision ground system from below. It analyses plantation records, the Port of Spain Gazette, government slave punishment returns, planter and imperial correspondence, slave codes, and enslaved people’s legal complaints from the nineteenth century to provide a more detailed portrait of the challenges of food cultivation under slavery in the years leading to abolition. Foregrounding scarcity as the common experience in the island’s provision ground system, it argues that enslaved labourers risked punishment to deploy a range of adaptive and sometimes illicit labour and land management strategies to properly cultivate their grounds under the constraints imposed upon them by plantation authorities. Furthermore, it shows how in the amelioration era, despite the odds being stacked against them, enslaved people found ways to strategically negotiate the office of The Protector of Slaves to retain rightful access to productive land and to protect their cultivation time and produce.