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This paper examines to which extent the Joseon-Ming relationship showed a very different development during the Zhengtong era (1436-1449) compared to the Yongle- Xuande era (1403-1435). It is argued that Emperor Zhengtong’s enthronement brought about a stabilization of the Joseon-Ming relationship. Both Youngle and Xuande Emperors took great interest in Joseon. They sought Joseon women as concubines for the imperial harem and found delight in Joseon food and music. Falcons and hounds from Joseon added a special touch to the emperor's hobby of hunting. Those who were in charge of running the Emperor’s errands were the eunuchs. Two eunuchs, Huáng Yăn, serving under Emperor Yongle, and Chāng Shèng, serving under Emperor Xuande, frequently visited Seoul over a period of more than 30 years. The emperor's orders in most cases were not written but oral messages. Thus, the instructions could remain unnoticed by the officials of the outer court. The Joseon court faced great difficulties trying to match the personal tastes of the two emperors, who at the same time were profligate, so that King Taejong and Sejong struggled hard to meet the greedy eunuchs’ demands each time they visited Seoul. The benefits, however, where not totally one-sided. Joseon received considerable help by the eunuchs in dealing with sensitive diplomatic issues. Behind the scenes, the eunuchs played a tremendous role in smoothing out the two countries’ relations, which during the preceding Hongwu era (1368-1398) had scarcely seen untroubled days. The situation changed dramatically with emperor Zhengtong’s accession to the throne. The young Emperor, who had just passed the age of seven payed little attention to Joseon. The grand empress dowager, who served as the regent, and wise men of the outer court, including the Three Yangs, sent back a large number of women from Joseon who had been selected by the previous Emperors. The eunuchs that had previously bullied Joseon also fell out of favor with the new emperor and were never sent to Seoul again. The practice of undocumented, oral messages from the Emperor also disappeared. Emperor Zhengtong reminds us of the Tumu Crisis, bringing to mind the manipulations of the eunuch Wang Zhen. Fortunately however, the interests of both did not extend to Joseon. With Emperor Zhengtong’s enthronement, the Joseon-Ming relationship suddenly entered a stable stage without major occurrences. Bereft of the influential contact persons they could please with words and bribes, the Joseon envoys now had to prepare documents in due form and negotiate with the fastidious officials of the Ministry of Rites. This change can be solely attributed to the new emperor. Thus, there were times when the emperors took interest in Joseon and tried to satisfy their needs through diplomacy with Joseon, and other times when they did not show such engagement. In the Ming dynasty, foreign affairs effectively were the emperor’s personal business.