In 1850, a women's community was founded in Bolshaya Rakovka, which became the center of the "conversationalism" movement in Orthodoxy. This direction, known as secular elder teaching, got its name because its followers, in addition to attending church, organized non-liturgical gatherings called "conversations." One of the key virtues for the conversationalists was strict obedience to the elder, who determined the entire way of life for his followers.

The community's abode was built not far from Bolshaya Rakovka in the village of Krasny Gorodok. By the decree of the Holy Synod on August 7, 1886, the community was transformed into the Rakovo Holy Trinity Women's Monastery.

During the existence of the monastery, five churches were erected. The first wooden, warm house church of the Trinity was built in 1863 and housed the main shrine of the monastery, the icon of the Mother of God "The Seeking of the Lost." By 1900, the church had fallen into disrepair, and in 1902, the construction of a new stone warm house church in honor of the icon of the Mother of God "Joy of All Who Sorrow" began, consecrated on October 13, 1905. A bell tower was located in front of the church.

On May 25, 1876, a stone cold church in honor of the Dormition of the Mother of God with a stone bell tower was consecrated. In the mid-1890s, with the funds of merchant N.P. Maslennikov, a three-altar stone warm Trinity church with a bell tower and refectory was built. The main altar was consecrated on May 20, 1895, the right chapel on May 22 in honor of the icon of the Mother of God "The Seeking of the Lost," and the left chapel on May 23 in honor of Nicholas the Wonderworker.

There was also a wooden cemetery church on a stone foundation in honor of All Saints, built in 1866. Due to its dilapidation, it was dismantled in 1882, and a new church was built, consecrated on September 8, 1884. In 1901, the church was moved to the village, and a chapel was erected in its place.

The main shrine of the monastery and the entire Samara diocese was the miraculous icon of the Mother of God "The Seeking of the Lost," gifted in 1850 by Anna Ivanovna Kadyshova. According to legend, the icon floated down the Volga to Saratov in 1666 and was revealed to the local voivode Kadyshov, which was accompanied by his healing and the exposure of the church property thieves. The icon was passed down in the Kadyshov family and was handed over to the monastery by Anna Ivanovna, the abbess of the Rakovo community. After the monastery was closed, the icon disappeared, but in 1954 it was transferred to the Protection Cathedral in Samara, where it remains to this day.