This article explores the complexities of cultural mediation between European missionaries and East Asian literati through an analysis of História da Igreja do Japão, written by the Jesuit João Rodrigues in early seventeenth-century Macao. Focusing on its astronomical and cosmological content, the study shows how Rodrigues engaged with Chinese and Japanese cosmologies, employing European Scholastic concepts to interpret unfamiliar ideas. In response to the negative reception of traditional European worldviews by Chinese authorities, he came to recognize the limitations of the Aristotelian-Ptolemaic framework. A key example is the rejection of solid celestial spheres, which prompted Jesuit authorities in Macao to adopt the theory of celestial fluidity in their philosophical curriculum. This strategic adaptation, championed by Cristoforo Borri, demonstrates the mutual nature of intellectual exchange. Jesuit missionaries not only introduced European scientific concepts to East Asia, but were also shaped by the cosmological perspectives they encountered. As such, the Jesuit policy of accommodation to Chinese culture paved the way for a more complex relationship between cultures, rather than a unilateral transmission of knowledge.