The Holy Spirit Novosil Monastery has been known since 1619, although it likely existed earlier. In 1637, it was destroyed and burned by the Crimean Tatars, who took 270 people captive from the monastery's lands.

In 1644, Tsar Mikhail Fyodorovich visited the monastery at the request of Igumen Simon, who advocated for the strengthening of the Novosil fortress and defensive structures against the Crimean Tatars and Nogais.

According to the land survey book of 1685, the monastery had one wooden church of the Holy Life-Giving Trinity with an altar dedicated to Saint Nicholas the Wonderworker, to which a refectory and porch were attached.

In 1764, during the secularization reform, the monastery was closed, and the church became a parish church. However, in 1767, thanks to the petition of local landowners, the monastery was reopened and classified as a non-staff monastery.

In 1770, a stone Cathedral Church was built, and in 1780, a stone Church of the Exaltation of the Holy Cross. Since the mid-18th century, a school operated at the monastery, which became a spiritual school in 1805 and was later moved to Novosil.

In 1821, a church in honor of Saint Nicholas was erected, and in 1844, a church in honor of the Savior Not Made by Hands. In 1925, the monastery was closed, and in 1934, two churches were blown up. Only the Church of the Holy Life-Giving Trinity survived, which was used as a warehouse.

During the Great Patriotic War, the Church of the Holy Life-Giving Trinity was severely damaged, with only the central part with a partially destroyed dome, the altar, and some structures of the refectory remaining. After the war, it continued to be used as a warehouse, and a machine yard was established on the monastery grounds.

The revival of the monastery began in 2004 with the blessing of Schema-Hegumen Ilya (Nozdrin) from Optina Pustyn. On December 27, 2005, the Holy Synod officially revived the monastery, although most of the buildings were destroyed.

Since October 2007, the brotherhood of the monastery has been engaged in spiritual care for the construction of the Church of the Korsun Icon of the Mother of God in the village of Korsun, Oryol region. In 2010, construction continued on the western and southern parts of the monastery fence with watchtowers and a chapel, and the southern part of the fence with a platform began to be erected. Restoration of the Church of the Holy Life-Giving Trinity continues, along with the construction of the temple complex, the laying of gas pipelines and heating networks, as well as the improvement of the monastery grounds.