The presented article attempts to consider the peculiarities of the stay of political prisoners in the Russian Empire in places of deprivation of liberty associated with serving the sentence established by the court. In particular, it is about the political prisoner Leonid Vasilievich Orlov, who was convicted for revolutionary activity and, being in Vladikavkaz regional prison in 1909, tried to resist the prison administration, which, in the specified period, toughened the regime of imprisonment, in connection with the consequences of the events of the First Russian Revolution (1905-1907). Orlov L. V. tried to defend his civil rights and the dignity of other political prisoners, considering this process as a continuation of the struggle against tsarism and revolutionary activities to which their lives were devoted. The article shows the conditions of convicts and prison administration, reveals the life and manners that reigned in certain places of deprivation of liberty in the penitentiary system of the Russian Empire of the early twentieth century, where not the least role, as it often happened, played the personal factor of a particular administrator (in this case, the head of the prison).