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The notion of accommodation, or the adaptation of one’s message to one’s audience, has been regarded as a central feature of the Jesuit way of proceeding at least since the seventeenth century. In recent years, scholars have come to understand accommodation as a rhetorical principle, which—while rooted in the rules of classical oratory—permeated all the works and ministries performed by the Jesuits of the Old Society. By comparing the theoretical notions about accommodation and the advantages and risks of adapting both the Christian message to native cultures and vice versa, this paper shows how and under what conditions the Jesuit missionaries were able to translate this rhetorical principle into a proselytizing praxis. By focusing on the examples of José de Acosta in Peru, Matteo Ricci in China, and of those Jesuits working in the missions in Paraguay and Chile, this essay will show how the needs in the missionary field superseded and overruled the theoretical requirements set beforehand. They revealed the ways in which the political and cultural context in which the missionaries operated determined the negotiations needed in order to achieve a common ground with their would-be converts if their mission was going to happen at all.