Monk Herman came from the town of Serpukhov, a short distance from Moscow. At the age of 16 he entered the Holy Trinity Sergius Hermitage, located on a Finnish bay about twelve miles from St. Petersburg. At that time St. Sergius Hermitage was attached to St. Sergius Lavra near Moscow and was governed by superiors sent from the Lavra. Father Herman lived in the St. Sergius Hermitage for some five or six years and later moved to Valaam Monastery situated on Lake Ladoga.

In the second half of the 18th century the boundaries of Holy Russia on the north were being enlarged with the activity of Russian promyshlenniki (scouts and pioneers). The Aleutian islands were discovered. With the discovery of these islands there was found a holy need of the evangelical light for the wild inhabitants there. For this holy task, with the blessing of the Synod, Metropolitan Gabriel entrusted Elder Nazarius, the Abbot of Valaam, to select capable men from among the Valaam brethren. Ten men were chosen, including: Archimandrite Ioasaph, Hieromonk Juvenaly, Hieromonks Athanasius and Macarius, Hierodeacons Stephen and Nektary, monk Ioasaph (tonsured into small schema), and Father Herman. In 1794 those chosen men left Valaam monastery for their appointed destination. With holy zeal the evangelizers quickly spread the evangelical light amidst the new sons of Russia. Several thousands of people accepted Christianity. A school was founded to educated the newly-baptized children. A church was built where the missionaries lived.

But by the unfathomable ways of God the general success of the mission was not long standing. After five years of his greatly profitable activity, the head of the mission, Archimandrite Ioasaph (who had been raised to the rank of a bishop) and his whole suite drowned. Before him, the zealous Hieromonk Juvenaly was vouchsafed a martyric crown, while others one after another left the mission. Finally there remained only Father Herman, and it was to him that the Lord sent grace to labor longer than all his co-brethren in enlightening the Aleuts.

Father Herman's place of residence was Spruce Island, called by him "New Valaam". The island is separated by a strait two miles from Kodiak Island. Spruce Island is not large and is all covered with forest. In the middle of it there runs a small river into the sea. Father Herman chose this island by himself as a place for his own seclusion, and dug there with his hands a cave in the ground and spent his first whole summer in it. By winter the Russian American Company built a cell for him near his earthen cave. He lived in this cell until his death, turning the cave into a place for his repose as a grave. Not far from the cell there rose a wooden chapel and a little wooden house for his school for the orphan Aleut children. He himself taught them the Law of God and church singing. And here he labored for more than 40 years, suffering slander and persecution for his fearlessness in the face of oppression.

Father Herman reposed in the Lord on November 15/28, 1836 at the age of 76.