Around the year 2000, members of the Teutonic Order were once again facing a financial crisis with a debt burden totalling some 364 million German Marks. Debt registers, handfasts and notes of indebtedness relating to the Teutonic Order in Prussia have survived from as long ago as the Late Middle Ages, documenting aspects of debt management and the repayment of debt claims by the Order's mercenaries after the Second Peace of Thorn. This study is the first to elaborate on debt management in the Order's lands during the upheaval after 1466. The edition of Ordensfoliant 259 and 261 plus additional material from the Secret State Archives of the Prussian Cultural Heritage Foundation, Berlin, is supplemented by the transmission history from the Königsberg Archives focusing on the mid-20th century.