In the "Description" of the monastery, Archimandrite Anatoly indicates that according to a report from 1764, submitted by the Oboyansk monastery to the Treasury Office, the church in honor of the Sign of the Most Holy Theotokos was made of stone both inside and out, and was in good condition, having been built on donations. Until 1850, the tent of the bell tower of the Sign Church was adorned with a crown topped with a small cross instead of the usual cross. Archimandrite Anatoly suggested that this crown might symbolize the contributions of the founders or royal gifts during the construction or renovation of the church. In 1850, a storm blew off the crown, and it was replaced with an eight-pointed cross.

On June 21, 1853, a project for the reconstruction and expansion of the church in honor of the Sign of the Most Holy Theotokos in Oboyan was approved. As a result, the church received two extensions and became three-altar: the main altar remained in honor of the icon of the Sign of the Most Holy Theotokos of Kursk, with an altar on the north side in honor of Saint Nicholas the Wonderworker, and on the south side, the Conception of Saint Anna. The reconstruction was financed by the Oboyan landowner Varvara Nikolaevna Krylova.

In 1877, Archimandrite Bonifaty informed the Kursk bishop Sergey about the need to replace the old dome of the church. By the bishop's order, the redesign of the dome was entrusted to the diocesan architect A. N. Yeremeyev. On March 14 of the same year, the Kharkov merchant K. E. Grinvald contracted to install new floors and doors, replace the dome, and add four more domes, as well as plaster and paint the walls with water-based paints, which he completed.

The church had six bells, the largest of which was installed during the tenure of Archimandrite Tikhon and sacristan and hieromonk Pimen in 1851. In the northern chapel, there was a copy of the miraculous icon of the Mother of God of Tolga.