Privateering both Christian and Muslim was an old practice in the Mediterranean dating back to medieval times. The presence of the Virgin Mary, especially, has a particular prominence. Since the medieval period, the Virgin had been an ever-present ally of the Christians during their confrontation with the Muslims. The iconography of a group of people seeking refuge under the cloak of the Virgin Mary was linked, in particular, with the representation of the Virgin of Mercy and had been very popular, especially in Italy, since the thirteenth century. The paintings analysed offer some significant examples of how the iconographical texts produced to celebrate and publicise the activities of the ransoming institutions represented an important visual counterpart to the various written texts on captivity and how they emphasised the danger of captives converting to Islam. All the paintings contain similar elements but also significant variations.