On June 27, 1248, the new religious family received canonical recognition from Pope Innocent IV under the name of "Order of Saint Benedict of Montefano," consisting of the hermitage of Montefano (diocese of Camerino) with the dependent "churches" of Santa Maria di Grottafucile (diocese of Camerino), San Marco di Ripalta near Rocca Contrada (now Arcevia) (diocese of Senigallia), and San Bonfilio di Cingoli (diocese of Osimo). The original of this important document, known as the " privilege of confirmation ," has not survived: the historical archive of the Silvestrine Congregation contains an authentic copy made from the original on April 3, 1251, in Cingoli, "by order of Brother Silvestro, prior of the hermitage of Montefano." After 1248, Silvestro founded the monasteries of San Bartolo della Castagna near Serra San Quirico, of San Pietro del Monte near Osimo, of Saints Marco and Lucia di Sambuco near Valfabbrica (PG), of San Tommaso di Jesi, of San Bartolo(meo) near Rocca Contrada (today Arcevia), of San Giacomo di Settimiano in Rome, of San Benedetto in Perugia and of San Giovanni in Sassoferrato.

This historic papal decree, issued by Pope Paul V on September 23, 1617, marks a major milestone for the Sylvestrine Congregation by formally establishing their monastic presence within the city walls of Osimo—the birthplace of Saint Sylvester. Prompted by the citizens of Osimo who deeply desired the monks' spiritual guidance, theological teaching, and pastoral care, the Pope took the significant legal step of suppressing the neighboring parish of Saint Andrew, transferring its parishioners to a nearby church, and permanently granting the entire church property, rectory, and sacred relics to Abbot General Sebastian Fabrini and the Sylvestrine monks for the immediate expansion of their monastery.

The structural hierarchy of the Sylvestrine Benedictine Congregation uniquely balances centralized global leadership with local monastic governance. At the highest level, the entire international order is governed by the Abbot General, alongside a Vicar General and the General Council. Geographically, the congregation is organized into distinct Provinces, which are formed when a group of autonomous, self-governing monasteries are brought together within a specific territory; the head of such a province is known as the Conventual Prior. At the local level, individual monastic houses within a province are led by a Prior or Superior. 

The oldest depictions of the Congregation's coat of arms are found in two mid-15th-century codices, which belonged to Prior General Stefano di Antonio da Castelletta and are now held respectively in the Staatsbibliothek der Stiftung Preussischer Kulturbesitz in West Berlin and the British Library in London. This coat of arms consists of a Gothic shield surmounted by a miter. In the shield's field rises a mountain with three peaks: behind the central, highest peak, a precious crosier appears, and two rose stems emerge from its sides. It was most likely adopted following the papal bull Exposcit tuae devotionis of October 30, 1449, with which Pope Nicholas V (who was in Fabriano at the time) granted Prior General Stefano di Antonio da Castelletta and his successors in the government of the Order the use of the pontifical insignia.