This chapter examines the decrease in the value of money in the Low Countries during the fifteenth and sixteenth centuries following the death of Charles the Bold, the last Duke of Burgundy from the House of Valois. His death allowed the emerging Habsburg regime to take control of Burgundy. During the years of crisis, revolts against the regime and the ensuing civil war contributed to the destabilization of trade and the economy. The chapter looks into the litigation records of the period, dealing with the payment of renten—rents or annuities. It examines how cities, mainly as debtors of such rents, were affected by the instability of currency rates brought about by the conflict. This instability was mainly due to the progressive debasement of the currency. Another factor was an ordinance passed by Emperor Maximilian I in 1489, which revaluated the currency, sparking disputes among creditors and cities.