The article examines the specifics of the monastery as a social institution within a distinct society—the Cossacks. In the public consciousness, a monastery is traditionally perceived as a closed ecclesiastical institution, where monks pray in the church and cells, interacting little with the outside, secular world. However, in the "Cossack" self-supporting monasteries examined in this article, the situation was somewhat different. These monasteries performed a variety of functions: liturgical, social welfare, socio-political, depository, patrimonial (ownership), settlement (monastery-household), charitable, and archival. According to the authors, frontier and gender concepts allow us to view a number of issues of monastic life and the significance of monasteries in social space from a slightly different perspective, as the southern Russian frontier (where the Cossacks emerged) differentiated monasteries into two types: those located directly within the territory of the Don Cossacks and those established outside it. Gender-specific "Cossack" monasteries distinguished themselves by their social and charitable functions: in the male version, they accepted new residents from among the elderly, sick, and disabled Cossacks; in the female version, residents included Cossack widows left without their breadwinners, and young women of Cossack descent, who found themselves outside the social sphere, mostly at the behest of their fathers. This, in another way, characterises the warrior-like religiosity of the Don Cossacks. Although God equalised men and women in the right of faith and prayer, the embodied male faith of the Cossacks, a sign of trust in a situation that occupies an important place in traditional Cossack culture, to a certain extent counters the female conspiratorial mentality of Cossack women, with its belief in prayer, in conspiracy, and in atonement for the sins of not only their own but also those of their beloved male warriors. Comparing historical Cossack monasteries, both male and female, with modern monastic communities located in historically Cossack regions, the authors conclude that the latter differ significantly from their predecessors. This raises the question of the retrospective adoption of the previous positive social and cultural experiences of "Cossack" monastic life.