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By the end of the sixteenth century, Japan and the Philippines established their first commercial and diplomatic relations, and during the Keichō era (1596–1615) an attempt of cooperation between Madrid and the government of Tokugawa Ieyasu (1598–1616) was planned. This allowed the Spaniards to foster their trade in Japan and to favor its penetration by missionaries. This volume discusses the different phases of the process of diplomatic/commercial and missionary relations within the context of the internal transformation of Japan and its ambitions for regional influence in Asia, on the edge of the Sinocentrism of the Ming Dynasty. It also analyzes the context of institutional and legal restrictions of the expansion of the Philippine archipelago as well as several factors that eventually led to the failure of the Hispano-Japanese cooperation and to the gradual disappearance of all kinds of formal contacts with Japan in the second decade of the seventeenth century.