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The purpose of this paper is to consider the establishment of the tosenbugyo 唐船奉行 to regulate foreign relations, and the reason why Ino-Yamato no kami-Sadatsura 飯尾大和守貞連 was appointed as the first tosenbugyo. In the fourth year of Eikyo 永享 (1432), the diplomatic relations, which featured the tally trade (勘合貿易) between Japan and the Ming dynasty and were discontinued after the death of the third Muromachi shogun Ashikaga Yoshimitsu 足利義満, were then restored by the sixth shogun Ashikaga Yoshinori 足利義教. After Yoshinori's time, the totosen 渡唐船 (the fleet of the ships from Japan to Ming China) consisted of the ships belonging to three different kinds of owners: the Muromachi shogun, temples, and the shugo daimyo. According to Mansai Jugo Nikki 満済准后日記, the system of the tosenbugyo was established in 1434 (永享6年) to mediate all the business about the tally trade between the ship managers, the gozan-monks 五山僧, and the Muromachi shogun as monarch of Japan. The first main (tanto) tosenbugyo was Ino Sadatsura, who was the bugyonin (one of the shogun's executive officers) in the Muromachi period. The Ino family, especially the Yamato branch, the Kaga branch, and the Hizen branch, were influential among bugyonin called gozen satashu 御前沙汰衆 (direct judges), and were promoted by the Ashikaga shoguns. The main tosenbugyo and the sub tosenbugyo (aibugyo) were appointed from the three branch of the lno family for generations. The tosenbugyo's regular work can be devided as follows: (1) to defend the trading ships around Japan, (2) to procure export goods, (3) to mediate among the Muromachi shogun, the ship managers and the Gozan-monks (4) to manage the tallies. In addition, Ino Sadatsura also conducted negotiations with the diplomats of the Li dynasty as a representative of the Muromachi shogunate. It had been impossible for a government official to deal with the diplomatic issues during the Yoshimitsu's reign. The diplomacy of the Muromachi period particularly valued the trade and it affected domestic politics. Tosenbugyo did not play such an active part in Muromachi diplomacy as the Gozan-monks did, but it is significant that the Muromachi shogunate was the first organization to appoint the executive officers of the samurai class to high positions in its diplomatic organization.