The monastery was founded by Paul, a hermit and disciple of Sergius of Radonezh. Paul, born in Moscow in 1317, left home in his youth to avoid an unwanted marriage imposed by his parents. At the age of 21, he took monastic vows and went to Sergius of Radonezh. By his blessing, Paul lived in seclusion near the Trinity Monastery for 15 years. Then Sergius blessed him to establish his own monastery, as a sign of which he gifted a forged copper cross, which was kept in the Obnorsky Monastery until the fire in 1909. In 1389, Paul built a cell for himself near the monastery of Dionysius of Glushitsky, but soon left it at the latter's request. He went to the Komel forests, where he lived for three years in a hollow of a linden tree, which was preserved in the monastery. Later, Paul arranged a cell on the right bank of the Nurma River, around which hermits began to settle. According to his life, in 1414, after a vision, Paul appealed to Metropolitan Photios for permission to establish a monastery but was denied. However, after a vision of the metropolitan, Paul received permission, and on the left bank of the Nurma, a wooden Trinity Cathedral was built, and a communal monastery was founded. Paul appointed his disciple Alexius as the abbot, while he continued to live in his cell, visiting the monastery on holidays. His spiritual mentor was Sergius of Nur, in memory of the meetings with whom a chapel was built between the Paul-Obnorsky and Spaso-Nur Monasteries. After his death in 1429, Paul was buried on the southern side of the Trinity Cathedral.

By 1764, the monastery had 28 monks, 1964 monastery servants and peasants, significant areas of arable land, meadows, forests, and fishing grounds. The monastery belonged to the third class with an abbot's administration. It was left with little arable and meadow land, fishing rights, and a salary was assigned. In 1867, a Resurrection skete was founded on a high hill near the monastery. In the mid-19th century, there were 12 monks living in the monastery. In 1909, the monastery suffered from a fire, in which the cross gifted to Paul by Sergius of Radonezh melted. In 1917, there were about 80 inhabitants in the monastery.

The last abbot was Archimandrite Nikon Chulkov. The monastery was closed in 1924 by the decision of the Gryazovets District Executive Committee. In the 1920s-1930s, the Trinity Cathedral, temple buildings, bell tower, and fence were destroyed. The territory of the monastery housed a pedagogical station, a school, and an orphanage. In 1945, a children's sanatorium opened, followed by a regional sanatorium-forest school.

The monastery was returned to the church in 1994. From 1994 to 2003, it was a dependency of the Spaso-Prilutsky Monastery. On June 5, 1999, the refectory church of the Assumption was consecrated. Since 2003, by the decree of the Synod, the monastery became independent. The abbot appointed was Igumen Amphilochius Kuznetsov, previously a resident of the Spaso-Prilutsky Monastery. There are 4 brothers living in the monastery, about 5 workers, and hired staff. A carpentry workshop operates here, bread is baked, and there is a small library.

Funds from the Vologda region budget are allocated for the restoration of the monastery. Scientific and project work has been carried out for the restoration of the bell tower of the Assumption Church. Since 2009, the construction of a wooden bell tower, restoration of the Holy Gates, part of the monastery walls, and towers has been underway.