Matteo di Giovanni was one of the most highly regarded painters in Siena during the 15th century. Like Venice, Siena remained under Byzantine artistic influence well into the 15th century witnessed here in the continued use of a gold background and the elaborate gold brocade of the Virgin’s dress; however, the influence of Italian Renaissance naturalism can be seen in the figures, particularly the face of St. Sebastian. The painting is a private devotional image probably painted for a wealthy Sienese family given the inclusion of the patroness of Siena, St. Catherine. St. Sebastian is present as protector against the plague. As an aid to devotion, the Virgin’s halo is inscribed ‘REGINA CELI LETARE’ (Queen of Heaven Rejoice) from the beginning of the Easter antiphon, and on her collar is written ‘AVE MARIA GRATIA’ (Hail Mary full of Grace) (Luke 1:28).