The article on the basis of archival material drawn by the author from the funds of the State archive of the Russian Federation, Laws of the Russian Empire and other normative legal acts of the Russian state considers the specifics of the prisoners who work in penitentiary establishments of Western Siberia, the formation of the system of labour remuneration, analyzes the productive capacity of penitentiary institutions. The article considers the change of the attitude to work as a punitive measures impact on the prisoner in the prison system in the Western Siberia and shows the formation of educational and labour impact on the identity of the prisoner; the impact of attitudes on the possibility of granting him parole. The author on the example of Tomsk № 1 detention division shows the use of prison labour in different periods of Russian history, creation of new productive facilities, the financing of the manufacture of commercial capital, attempts to create a system of self-sufficiency of life prisoners, with the partial filling of the expenditures for their maintenance. Aspects of inheriting by the Soviet authorities the criminal-executive policy of the prerevolution, revolution and the Civil war period practices in the organization of work of the convicts is discussed.