This paper analyzes Japan’s efforts to reach out to the Islamic world, particularly to the Middle East, in the first half of the twentieth century. It pays particular attention to the hajj by Japanese Muslims from the 1900s to the end of the 1930s because the hajj neatly captures the changing ways in which the Japanese interacted with state and non-state actors from various parts of the Islamic world including Central Asia, China, and Saudi Arabia. Through this focus, this study seeks to explain the nature of cross-cultural encounters between Japan and the Islamic world and contribute to the growing historiography of transnational and transregional history. The following is the narrative presented in previous studies. After the Russo-Japanese war, some Japanese pan-Asianists recognized the significance of gaining support among Muslim populations, while Muslim revolutionaries became aware of Japan’s potential as their sponsor against colonial powers, in particular tsarist Russia. Before long, the first Japanese Muslim accompanied a Tatar Muslim on a pilgrimage to Mecca. By the 1930s, under the pretext of uniting Asian peoples of color from East Asia to the Middle East against the materialistic white race in the West and the communist Soviet Union, winning Muslim hearts became a vital component of the official policy of the expansionist Japanese Empire. This perspective concentrates almost exclusively on Japan’s strategic and geopolitical interests in facilitating its interactions with Muslims. By using a variety of primary sources including memoirs of Japanese pilgrims, Japanese and British diplomatic documents, publications of Islam-related organizations in Japan, and Arabic and Persian periodicals, this work suggests that the driving force of Japan’s encounters with the Islamic world was not limited to strategic interests and geopolitics. Economic motives and the need to strengthen commercial ties also played an important role in the cross-cultural encounters. In fact, Japan’s economic motives in the Islamic world, particularly 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. Furthermore, this study suggests that the economic encounters were fairly interactive. Muslims in the Middle East were active participants in their interactions with Japan, just like Central Asian and Indian Muslims were.