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The medieval castle withstood many a siege. First and foremost, the one by the army of Ladislaus of Durazzo, king of Naples, who in the first few years of 1400, decided to expand the borders of his kingdom and set up an encampment in the Val di Chiana prior to completing the conquest of the Republic of Siena and the Duchy of Florence. In 1455, the castle was subjected to a new siege by mercenaries of the Compagnia di Ventura led by Jacopo Piccinino from Perugia, but once again managed to resist. In 1467, the municipality of Sarteano came to an agreement with the ruling powers of Siena which provided diplomatic and military protection by the Republic of Siena in exchange for the municipality of Sarteano becoming part of the Republic.