The miraculous icon of Theotokos Proaggellomeni is placed in the chapel of the Dormition of the Virgin Mary. Its history is related to the period of the union of the two churches and the ensuing conflict with the papacy in the 13th century when John Vekos was Patriarch of Constantinople.
According to tradition, the icon was in the possession of a hermit monk who used to pray before it, chanting the Akathist Hymn. One day, while addressing the Virgin Mary with "Rejoice, O Bride unwedded", he heard from the icon the reply "Rejoice, old man". The monk was startled and remained staring in amazement. The voice of the Virgin Mary reassured him and explained the reason for her revelation. She told him that papal soldiers were coming to the nearby monastery determined either to dominate it by imposing their faith or to committee a slaughter. She instructed him to go quickly to the monastery in order to inform the abbot and the other monks of the impending danger. So he did. Arriving at the entrance, he found the icon of the Most Holy Theotokos preceding him. He venerated it and informed his brothers, as he had been asked to do. Some of them hid away from the monastery, while the abbot and 25 monks closed themselves in the tower, waiting for the enemy and determined to die for their faith. When the soldiers arrived, they first tried to persuade the monks to accept the union of the churches and open the gates. However, in the face of their stubbornness they quickly became violent, setting the monastery on fire and burning everything, including the monks who were locked in.
These martyrs are commemorated until today on the 10th of October. The icon is still venerated on the 29th of July and on the 15th of August, during the celebration of the Assumption of the Virgin Mary. The litany that takes place ends at the monument of the 26 martyrs. During the divine liturgy it is also chanted the sequence written for Our Lady of the Annunciation.
Its name comes from the fact that the danger that threatened the monks was foretold. She is also sometimes referred to as Theotokos of the Akathist, for the answer she gave to the monk who chanted the greetings before her, and as Theotokos of Chaerovo, because she answered the old man's prayers with "Rejoice" which in Greek is “Χαίρε” (“Chaere”).
As far as her iconographic type is concerned, the structure of Theotokos Hodegetria is followed. The Virgin Mary holds Jesus in her left hand, while her right hand is at the chest level. The Divine Infant blesses the faithful with His right hand, while with His left hand He holds an open Gospel. The relief frame covering the icon is particularly rich and imposing. It is adorned with elaborate designs and precious stones. At the bottom there is an inscription with details of its origin.