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One of the earliest examples of Jesuit spiritual writings is the Esercitio della vita christiana of Gaspar Loarte, S.J. First printed in 1557, the work found massive editorial success, eventually being reprinted forty-four times and translated into five different languages in the early modern period. By analyzing correspondence between Loarte and his superiors in Rome, including Ignatius of Loyola, regarding the Esercitio, this paper seeks to recreate the first generation of Jesuits’ own understanding of devotional literature — what its purpose was, what it should be contain, and how it should be printed and disseminated. I argue that although the Esercitio does not bear many similarities to the quintessential work of Jesuit spirituality, the Spiritual Exercises, it is instead rooted in the active pastoral ministry that characterized the early Society of Jesus, growing organically out of their time spent preaching, teaching, and hearing confessions.