Before the masterful frescoes of Blessed Fra Angelico graced the cloister of San Marco, the Order of Preachers (Dominicans) possessed an artistic work of great character and heritage in the miraculous image of the Madonna of San Sisto in Rome, Italy.

This icon of Our Lady was thought during the Middle Ages to have been designed by Saint Luke the Evangelist and to have been painted by angels. Legend held that a holy man from the East brought it to Rome. There it was acquired by three brothers who were exiles from Constantinople, presumably because their adherence to orthodox Christianity, ran into conflict with an outbreak of monophysitism or iconoclasm. The image was placed in the Church of Santa Agata in Turn outside the Appian Way, which, in honor of the icon, became known as alternatively, Santo Maria in Turn and Santa Maria in Tempulo. Confirming parts of this medieval legend, modern historical study has indicated that this Madonna is of Byzantine origin and was venerated at least by the end of the fifth century.

When Saint Dominic was charged by Pope Honorius III to establish a reformed community of nuns at San Sisto in Rome, one of the communities from which nuns were voluntarily drawn was the monastery at Santa Maria in Tempulo. St. Dominic lavished his attention upon the nuns of Santa Maria, preaching to them and giving them spiritual direction. It was to each of these same women in 1219 that St. Dominic brought wooden spoons which he had carried on a journey from Spain. At that same time, he received the promise of the nuns that they would enter the new community of San Sisto. However, the mere possibility of the nuns moving from their monastery into a stricter community caused their relatives and friends to protest vociferously. After further entreaties from St. Dominic, most of the nuns agreed to join the new community of San Sisto.

The nuns placed one caveat on their promise: that the miraculous image of the Madonna in Santa Maria in Tempulo should also come with them. This was no ordinary request. Legend had it that in the tenth century Pope Sergius III tried to move the painting into the John Lateran Church, but it had returned miraculously to its original home. God seemingly wanted the painting to remain in Santa Maria in Tempulo.

St. Dominic was not daunted by the challenge. On the First Sunday of Lent, February 28, 1221, Our Holy Father gave the habit and received in his hands the profession of the nuns entering San Sisto. During the following night, St. Dominic carried the miraculous image of the Madonna to its new home at San Sisto. The painting did not fly back on its own accord, thus bestowing the divine seal of approval to St. Dominic's foundation.

The miraculous Madonna remained at San Sisto until 1575, when it was transferred to San Dominico and Sisto on the Quirinal where the nuns had relocated upon the urging of Pope Saint Pius V. After the monastery became the home of the Angelicum, the image was under the care of the Dominican friars for a time. In 1931, however, the image was placed in Santa Maria del Rosario e della Febbre a Monte Mario where the nuns had moved into a new monastery. The image was restored by Dr. Carlo Bertelli in the 1950's.