Determining the exact time of the foundation of the Assumption Monastery is difficult, and there are two main versions in the scientific community. The first suggests that the monastery was founded in the 8th-9th centuries by Greek iconophile monks who fled from Byzantium. They chose this location due to its resemblance to Athos, the availability of fresh water, and picturesque nature. The monks carved a temple and cave cells into the rock. The monastery was located on the border of the Christian and pagan worlds, allowing the monks to engage in missionary activities among local tribes. Archaeological finds of 6th-century Christian burial sites in the vicinity support this version, as believers needed churches for worship.

The second version dates the foundation of the monastery to the 15th century. It is possible that it was previously located at the southern gates of the Kırk-Or fortress, but after the fortress was captured by the Turks in 1475, it was relocated. This version was supported by the 19th-century scholar A.L. Berthier-Delagarde, referring to lost manuscripts. During the Turkish invasion, the monastery was not destroyed. Soon after, the capital of the Crimean Khanate, Bakhchisarai, emerged nearby, allowing ambassadors from Orthodox states to pray among their co-religionists. By the end of the 15th century, the monastery became the residence of the metropolitan. The Moscow historian Lyzlov mentioned that the Crimean khan turned to the Holy Virgin before campaigns. The monastery played an important role in supporting Christians during difficult times.

Over time, the monastery fell into disrepair. A letter from Prince Prozorovsky to P.A. Rumyantsev-Zadunaisky dated May 31, 1777, indicates that the church was in decline, and plans were made to build a new one, but these plans were not destined to come to fruition. In 1778, Metropolitan Ignatius called on Christians to leave Crimea, and many settled on the shores of the Sea of Azov, founding Mariupol. However, the monastery was not completely abandoned. In 1781, Greek priest Konstantin Spirandi resumed services in the Assumption Church. The monastery became a parish church, attended not only by local Christians but also by Russian soldiers. In 1800, the Cathedral of St. Nicholas was built in Bakhchisarai, and the monastery became deserted, remaining lively only on the Feast of the Assumption of the Mother of God. It was visited by members of the imperial family, including Alexander I and Nicholas I.

The revival of the monastery began in 1850 thanks to Archbishop Innocent. In 1850, the Assumption Skete was opened, consisting of three cave cells and a temple. The monastery had a general construction plan developed in 1848. In 1850, a bell tower was built, but the Crimean War hindered further development. The monks assisted in the hospital of the Russian army. After the war, the monastery was restored, and the Church of the Assumption of the Mother of God was repaired. The architectural appearance of the monastery included three tiers with various churches and buildings.

The lifestyle of the monks was austere; they worked to maintain the monastery. The number of monks grew, and in 1915 there were 30. In 1878, the monastery received a dependency in Simferopol. After the revolution, the monastery existed for several years but was closed in 1921, and a labor colony was established in its place. Most of the buildings were destroyed, with only the Assumption Church and the abbot's house remaining.

During the Great Patriotic War, the monastery again became a hospital. In 1944, wounded soldiers were treated here, and new burials appeared next to the graves of warriors from 1853-1856.

A new revival of the monastery began in 1993. The abbot's house and cave temple were returned to the monastery. Thanks to the efforts of Father Siluan and the parishioners, the monastery was gradually restored. The Assumption Church and staircase were renovated, and a bell tower was built.