After the suspension of tribute missions, Japanese pilgrim monks actively sought assistance from Chinese merchants for their travel and for acquiring scriptures and objects from the continent. Using two sets of private records written by merchants, which have never been explored in Western scholarship, this chapter shows how the pilgrim monks and sea merchants started to build a network both for transmitting Buddhist teaching and for profit-making. Correspondence between monks and merchants suggests that certain Chinese merchants traveled on a regular basis between the continent and the archipelago, and they therefore formed a close relationship with monks in Japan. The monks designated the merchants as their envoys, sending gifts and letters containing Buddhist-teaching inquiries to Chinese monks, while the merchants hoped to gain access to Japanese authorities via the monks’ introductions.