This article analyzes Japan’s efforts to reach out to the Islamic world, particularly the Middle East, in the first half of the twentieth century. It pays particular attention to the hajj by Japanese Muslims from the beginning of the twentieth century to the end of the 1930s because the hajj encapsulates the changing ways in which the Japanese interacted with state and nonstate actors from the Islamic world. Existing works on Japanese-Islamic interactions before 1945 have provided detailed analyses of Japan’s strategic and geopolitical interests in facilitating its interactions with Muslims. Building upon these works, this article stresses the significance of economic motives and the need to strengthen commercial ties in the cross-cultural encounters. In fact, Japan’s economic motives in the Middle East were closely intertwined with its strategic motives, and the two motives supplemented each other in fostering Japan’s desire to reach out to the Islamic world.