At the centre of this article is Giorgio Vasari’s Tavola della Concezione for the church of Santi Apostoli in Florence and its many derivations in sixteenth and seventeenth century Tuscany. Focusing on the novel iconography of the altarpiece, and in particular on the genesis and mean- ings of the theme of Adam, Eve and the Patriarchs represented in the lower section of the paint- ing as tied figures in the process of being liberated by the Virgin Mary, the essay highlights not only the ratio behind this theological invention and some of the wider meanings of the Christian theme of the liberation of original (biblical) humanity from sin, but also the incredible regional success of this pictorial invention authored by Vasari to represent the much contested theme of the Conception of the Virgin. While existent scholarship has already demonstrated that part of the iconography derives from previous solutions created in particular by Rosso Fiorentino, this essay will argue that the visual theme of the liberation of both the naked and dressed figures of the Patriarchs from the laces of sin, as chosen and developed by Vasari, can be interpreted, not only, as an ingenious solution for the iconography of the conception of Mary outside original sin, but also as a metaphor for artistic ‘conception’ and creation, execution, and success.