From the time of Ermak’s conquest in 1582, Siberia has both served and been envisaged as a carceral space, a land of exile and punishment. In the modern era, this image has proliferated and endured both within Russia itself and on the international stage. For many Russians and Westerners alike, Siberia has long provided fertile ground for mythmaking about Russia, and has become a byword for and synecdoche of political oppression and the evils of autocratic and totalitarian rule. In this thesis, I argue that representations of Siberian exile played a crucial role in transnationalising the Russian revolution during the decades prior to 1917. Throughout the nineteenth century, the image of Siberia as a vast prison camp – and, by extension, the birthplace of revolutionary heroes – was commonplace in the oral and literary traditions of Russia’s radical intelligentsia and amongst Anglo-American progressives alike. In both cases, Siberia represented an indictment of the Tsarist state and, to some extent, prefigured Russia’s post-autocratic future. From the 1880s onwards, a succession of Russian émigrés in Britain and the United States duly sought to capitalise on their hosts’ fascination with Siberia by publicising dramatic tales of political exiles’ mistreatment and heroism in captivity. Tracing the development of this discourse, I demonstrate that although it elevated several revolutionaries to international celebrity status and succeeded in securing considerable overseas support for their cause, it also exposed contradictions in how the revolution was understood inside and outside Russia. As Russian socialists used the rhetoric of punishment and protest to articulate their own ideological convictions, Britons and Americans romanticised and projected themselves upon the mythologised figure of the Siberian prisoner. In this sense, fin de siècle polemics over Siberian exile can be seen to anticipate Western anxieties over Russian oppositionists prevalent in our own time