The article analyses the functional status of the institution of bailiffs in the forts and settlements in the Upper Ob area from the position of genetic and systemic approach. Within the context of the administrative process, the display is made of the three key functions of bailiffs: defense and supply, administrative-economic and police. Bailiffs are considered as part of the administrative doctrine of Kuznetsks voivodes. Special attention is paid to the problem of the bailiffs’ crimes and to the administration in the forts and settlements in the absence of legitimate governance institutions. Illustrating his position by specific historical factors and events, the author proves the interdependent theses on the perception by the local supervised settlers and voivodes of bailiffs as the only legal and legitimate institution of the administration in the region; and creating of the situation of internal social tensions when bailiffs left the town. The author arrives at the conclusion about the fundamental strategic role of bailiffs in administration the forts and settlements in the Upper Ob area.