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Drawing on Piromalli's letters and accounts, this paper analyze the conversion strategies he adopted in his missionary work and what could be seen as a paradigm shift in his policy. In his Account of his Own Successes, written in 1637, Piromalli clearly embraced what at the time was a 'classic' approach: to discuss first the matter of the union with the local ecclesiastical hierarchies; then, when—as it often happened—this failed, to gather some disciples among the schismatics who would preach correct creed among local people on a more practical and day-to-day basis. However, in another account that Piromalli wrote in 1654, just a few months before being officially appointed the Archbishop of the Diocese of Nakhichevan, he claimed that although the Armenian 'clergy was already educated and enlightened in the Catholic truths', only the conversion of the wealthy Armenian merchant families of New Julfa could persuade other Armenians to embrace Catholicism. Since, as he wrote, 'all missionary efforts are wasted' in converting New Julfan Armenians, he maintained that it was necessary for the Pope to ask 'the Princes of Venice and Tuscany' to threaten the New Julfan merchants that they would be denied access to their ports, unless they chose to convert. This paper will consider this shift by discussing Piromalli's attempts to bring the whole Armenian Church into union with Rome, including his role in the union of the Polish Armenian Church. It will also analyze his embracing of a more Realpolitik approach in light of the emerging Armenian merchant colony of New Julfa.