This chapter focuses on three Japanese pilgrim monks who visited Northern Song China (960–1127) and had extensive interactions with Chinese emperors, court officials, and merchants. Monks’ diaries and other court records indicate that by the eleventh century, the authorities in both China and Japan were aware of the collaboration between monks and merchants and were even taking advantage of the newly formed network. Japanese aristocrats hoped to acquire desirable continental commodities via the monk-merchant cooperation, and Emperor Shenzong of the Song asked a Japanese pilgrim monk to bring his gifts and letter to the Japanese authorities.