Abstract: It has long been known that English Cistercian monasteries often sold their wool in advance to foreign merchants in the late thirteenth century. The abbey of Pipewell in Northamptonshire features in a number of such contracts with Cahorsin merchants. This paper looks again at these contracts in the context of over 200 other such agreements found in the governmental records. Why did Pipewell descend into penury over this fifty year period? This case study demonstrates that the promise of ready cash for their most valuable commodity led such abbots to make ambitious agreements ? taking on yet more debt to service existing creditors - that would lead to their eventual bankruptcy.