Domenico Beccafumi was present in Montepulciano in 1507 as certified by Andrea Giorgi's documentary research presented in this same volume of 'Prospettiva'. His presence coincides with the appointment of Lorenzo Beccafumi, the painter's protector, as podestà of the city of Poliziano. This allows us to link the artist with a canvas of 'Saint Agnese Segni' until now of uncertain attribution, conserved in the Civic Museum and Pinacoteca Crociani at Montepulciano. The painting, cut in length, was originally a gonfalone commissioned by the Commune as a votive object. Stylistic features − marked by the iconic mode of the type − evoke the culture of Pietro Perugino, who had arrived in Siena in 1506. According to Giorgio Vasari's 1568 biography of the Sienese artist, Perugino had fascinated Domenico in his initial years. Such peruginesca culture interwoven with early echoes of the young Raphael and of Leonardo himself links the canvas with a series of panels attributed until now to an anonymous painter known as the 'Maestro delle eroine Chigi Saracini', presumably active in Siena during the second decade of the Cinquecento. Anchoring this series of panels to the 'gonfalone poliziano' of 1507 allows us to give these works to the young Beccafumi and to date them at the beginning of the century. These years precede both Domenico's first stay in Rome and his execution of the Triptych of the Trinity, attested in 1513 for the Cappella del Manto in the hospital of Santa Maria della Scala. Among the most convincing pieces in the series are the three Chigi Saracini heroines − 'Giuditta', 'Cleopatra,' 'Artemisia' − preserved in the aforementioned Chigi Saracini collection in Siena, the 'Madonna and Child with the young Saint John' in a private collection in Florence, and the tondo of the same subject, in the State Museums of Berlin. Two coffin headboards in the Pinacoteca Nazionale of Siena complete this group of artworks; they depict 'Saint Augustine', 'Saint Galgano', 'Saint Paul' and 'Christ in pietà' and slightly precede the dossal for the hospital.