The small town, located at the confluence of the Syzran and Krymza rivers with the Volga, was founded in 1683 by the decree of Tsars Peter and Ivan Alexeyevich, as well as the Siberian and Kazan voivode Grigory Kozlovsky. It served as one of the fortresses protecting the Volga river route and the new lands of the Volga region from eastern nomadic raids.

The first inhabitants of the fortress, mainly soldiers and sergeants from Kazan, Cheboksary, Simbirsk, and other places, were predominantly Orthodox. Therefore, soon a cathedral church was built in the fortress in honor of the icon of the Mother of God "Life-Giving Spring." Chronicles from those years note that many soldiers were old and frail, wishing to become monks, but lacked the opportunity due to the absence of a monastery nearby. In May 1685, by the decree of the tsars, Elder Kirill was granted a charter to build the Ascension of the Lord Monastery, the Most Pure Mother of God of Smolensk, and Archangel Michael opposite Syzran, on the other bank of the Krymza River. In the spring of 1687, Elder Kirill moved the monastery to the town of Kashpir, located 8 versts from Syzran, leaving only a few people under the guidance of Elder Philaret at the previous site. The residents of Syzran did not want to be without a holy abode and in 1691 asked Patriarch Adrian for permission to build a monastery in honor of the Ascension of the Lord. After receiving the blessing, Elder Philaret began the construction of a wooden Ascension church, for which a small sum was allocated from the royal treasury. However, funds were insufficient, and the construction lasted three years. In 1694, a wooden church was built, and in 1695, the first inventory of the monastery was compiled, which housed seven monks.

The Ascension Monastery also became the first necropolis of Syzran. According to Russian custom, the deceased were buried near the church, while noble people were buried inside the temples. On the territory of the monastery near the Church of the Theotokos of Theodore, the first cemetery appeared. Here, builders of the fortress and monastery were likely buried. Among those resting in the cemetery are Prince Mikhail Vladimirovich Urusov and his daughter Princess Anastasia, as well as other notable residents of the city. In the Theodore Church, in 1790, Ekaterina Ivanovna Dmitrieva, sister of the poet and Minister of Justice Ivan Dmitriev, was buried. In 1844, the first manager of the Simbirsk diocese, Archbishop Anatoly Maximovich, was buried here, and in 1847, the monastery's abbot, Archimandrite German Pokhvalinsky.

At the beginning of the 20th century, the monastery was a prosperous estate. Its last abbot was Archimandrite Alexander, in the world Sergey Vakhatov. In 1923, he signed an act dissolving the monastery, after which all its buildings and properties were nationalized. Only the Theodore Church remained under the control of the church community, with its activities monitored by the authorities. In 1931, Archimandrite Alexander was exiled, and in 1937, he was shot on charges of counter-revolutionary activities.

In 1928, the Ascension Church was closed, and in the early 30s, the Theodore Church was also closed. In 1933, the monastery buildings were leased to the "Soyuzplodovoshch" combine. The monastery cemetery was destroyed, and factory buildings and a road were built in its place.

After a millennium of the Baptism of Rus, the revival of churches and monasteries began. In 1993, the administration of Syzran transferred the remaining buildings of the monastery to the Orthodox Church. In 1996, Archbishop Sergey consecrated the cathedral church, and monastic life resumed in the monastery. Services and prayers are held here, including before the icon of the Mother of God "Inexhaustible Cup" and penitential prayers for women.