This chapter examines Volkhovskii’s life from his third arrest in 1874 through to his flight from Siberian exile in 1889. Following his third arrest, Volkhovskii was held in various prisons, before being tried and found guilty of promoting revolution before a Senate Committee at the Trial of the 193 (1877). During his time in prison, Volkhovskii continued to write revolutionary poetry, something that he started during his earlier incarceration, as well as contributing extensively to legal journals on questions of education (including numerous poems written for children). Following his exile to Siberia, at first in an isolated village and later in Tomsk, Volkhovskii faced almost constant material hardship. He was however able to publish extensively, becoming the most prolific contributor to the journal Sibirskaia gazeta (Siberian Gazette), contributing numerous theatre review and short stories. While some of these were informed by a utilitarian aestheticism, promulgated in previous years by writers like Nikolai Chernyshevskii and Dmitrii Pisarev, Volkhovskii also developed a penchant for writing fantasies that often satirised bureaucratic corruption and the materialism of the merchant class. Sibirskaia gazeta was committed to fostering the development of Siberian self-consciousness, something that Volkhovskii echoed in many of own his stories and poems, reflecting his long-standing view that building national identity among minority groups could help to challenge the centralised system of bureaucratic rule that characterised the tsarist state. By the late 1880s, the material hardships faced by Volkhovskii were worse than ever, while his meetings with the American traveller George Kennan convinced him that he should move abroad in order to win international support for all those opposing the tsarist government.