Most probably in the late 1470s or early 1480s, the historically interested cardinal and patron Francesco Todeschini Piccolomini (1437/39–1503) requested the monk and humanist Hilarion of Verona (c.1444–c.1484) to revise an older Vita Caroli Magni with regard to its content and style, as the cardinal considered the text no longer in keeping with the times. Hilarion accepted the request and penned a new vita of the Carolingian ruler, relying heavily on the classical 9th-century vita of Charlemagne by Einhard, but also to some degree on the Vita Caroli Magni written in 1461 by the Florentine humanist Donato Acciaiuoli (1428–1478). Throughout the vita, Hilarion uses quotations from Roman authors, showing his attempt to provide his work an antique touch. The present study offers critical and annotated editions of the Vita Caroli by Hilarion of Verona as well as of the letter of order from Cardinal Piccolomini. Also included is a translation of the vita into German. In addition, an attempt has been made to place the text into its historical and intellectual context. It was possibly related to the religious and political debates during this period between the Holy See and Louis XI, King of France.