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In 1593, 1609 and 1616 three very different attempts were made by the rulers of Japan to establish formal diplomatic and trade links with Taiwan. The 1593 approach consisted merely of a letter that proved impossible to deliver, while the others involved sending well-equipped fleets to the island. Both the latter expeditions were led by prominent Christians in efforts that ultimately came to nothing, in spite of being backed up by very meaningful threats of military intervention. This paper argues that it was largely the nature of Taiwan itself that frustrated Japan's schemes. Taiwan had no overall ruler who could participate, willingly or not, in the accepted modus operandi that had been applied to Korea in 1592 and Ryukyu in 1609. This was an approach based on the tributary model. Instead Taiwan's fragmentary structure of aboriginal tribes laid it open to a more western-style form of development involving the establishment of a military base and colonisation, a means that was to be exploited by the Dutch in Taiwan a decade later to the astonishment and rancour of the Japanese. [ABSTRACT FROM AUTHOR]