Back around the fifth and sixth centuries, when a monk died, his confreres celebrated Masses for his soul for 30 consecutive days. Legend has it that 30 days after a certain monk died, his friend received a vision of the deceased, thanking everyone for praying for him. He was in a better place because of their Masses. It is important to note that this vision occurred after the 30th Mass was celebrated. This is the start of the tradition of having Gregorian Masses for a deceased person.
The Catholic Encyclopedia explains this ancient tradition as follows: “Gregorian Masses consist of a series of thirty Masses offered on consecutive days for the soul of a deceased person. They receive their name because of a story written by Gregory the Great (died 604) in the DIALOGUES (4:55; PL 77: 416-421) about a Monk who obtained release from Purgatory after thirty Masses were offered on his behalf. On two occasions, the Sacred Congregation on Indulgences (March 15, 1884; August 24, 1888) declared the confidence of the faithful in the efficacy to God’s mercy and good pleasure, and asserted their approval by the Church.”
picture from communio.stblogs.org
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