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The abbey of Monteoliveto Maggiore which stands atop a spur of the Crete Senese, the barren, rocky country southeast of Siena, is one of the most important and best preserved monastic complexes in southern Tuscany. It was founded by the prominent and well-to-do legal scholar Giovanni Tolomei (1272-1348), who resigned his post as podestà of Siena and renounced his worldly interests to take up the life of a hermit. He was joined by two other men from Siena, Ambrogio Piccolomini and Patrizio Patrizi. The three built themselves shelters in this hostile landscape and over the years still others were attracted to the fledgling ascetic community. On March 26, 1319, the Bishop of Arezzo, Guido Tarlati, confirmed the congregation as a new religious order.
The painting of the confirmation of the Olivetan rule in the monastery of Sant'Anna in Camprena, near Pienza, which was founded by monks from Monteoliveto in 1324, is part of a cycle painted by Sodoma in the refectory in 1503-04. In this scene one can see Tolomei, by now known as Bernardo, kneeling before the bishop on his throne in an open loggia, the rule in his hand.
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