The English, and later British, settlement of Bencoolen was first established in 1685 and remained in British hands, barring French wartime occupation, until 1825, when it was handed over to the Dutch in a territorial exchange. Bencoolen was even elevated to the status of a Presidency in the second half of the eighteenth century. Why did the English East India Company and British officials maintain a presence in Bencoolen for so long? This article makes the case that multiple, overlapping visions of commercial and agrarian transformation, including projects focused on pepper and sugar cultivation, sustained British efforts to govern and maintain Bencoolen as part of a larger, trans-oceanic network of territories. Such visions of Bencoolen's economic and imperial potential evolved in sync with equally persistent concerns about Bencoolen's failure to become a thriving settlement. Yet even amid constant anxieties about producing enough pepper, maintaining a sizeable population, and generating sufficient revenue, numerous British imperial agents located in London and Calcutta as well as Sumatra argued over whether the settlement was likely to remain a permanent failure and how the problems that dogged it might be resolved. Thus, even in moments when Bencoolen appeared to be a failed outpost on the periphery of a growing British Empire, its success or lack thereof commanded the attention of British ministers and East India Company servants. In calling for Bencoolen's elevation, subordination, or even abolition as a settlement, Britons contributed to a wide-ranging discussion of what constituted a valuable colony and, indeed, empire.