The sacred Tenderness Icon of the Most Holy Theotokos was painted and brought to the Pskov Caves monastery through the efforts of the devout Pskov merchants Basil and Theodore. It was transferred it to the town of Pskov in the year 1521, and was glorified by miracles of healing in 1524. The Tenderness Icon is especially honored as the protector of the city when it was besieged by the Polish King Stephen Bathory (1533-1586) in the year 1581. Both the Tenderness Icon and the Dormition Icon were glorified at that time.
The Tenderness Icon is also honored on October 7, the day when Pskov was liberated from Napoleon's invasion in 1812. Other days on which the Tenderness Icon is commemorated are: June 23, August 26, and on the Seventh Sunday of Pascha.