In 1238 Herman, now an old man, became ill and travelled to Salerno for his health. He died on 20 March 1239. Shortly after his passing the Teutonic Knights were faced with two major dilemmas. Firstly, with the end of the truce in the Latin East and the final preparations for a new crusade, they were required to render assistance to the Holy Land. At the same time, however, they were locked in conflict with the Rus in Livonia. The Order's new master, therefore, needed to decide how he would divide his institution's material resources. The second problem concerned the ongoing issue of the Order's relative loyalties to the papacy and the empire. This matter rose again to the fore in 1239 when Gregory excommunicated Frederick, provoking a new war between these protagonists. The emperor responded by moving to acquire a stranglehold on the papacy through the submission of the Italian cities. Once again the military orders were faced with a conflict of loyalties. To resolve this question, the Teutonic Order had to look to its new master, Conrad von Thüringen. Conrad's policy was very different from that of his predecessor and he shunned the previous position of diplomatic neutrality for one of allegiance to the empire, with significant consequences for the Holy Land.

Born in 1206, Conrad was the youngest son of Herman, landgrave of Thuringia. After his father's death in 1217, Conrad's older brother Ludwig succeeded to the title. Ludwig died in 1227, shortly after embarking for the Holy Land, leaving a young son to succeed him. Conrad and his brother Henry then became regents for their nephew, who was still a minor. During this regency, the two brothers followed the tradition of their forefathers and became patrons of the Teutonic Knights