In the short period between 1905 and 1911, the Middle East and Caucasus experienced three revolutions: the Russian, Iranian, and Ottoman. One of the key factors that helped shape and connect them was the circulation of revolutionaries – in the case of this paper, Armenians – arms, print, and ideas that crossed geographic frontiers and in the case of ideas intellectual and ideological frontiers, too. Ideologies, like socialism, made their way from the South Caucasus and Western Europe to Iran and to a lesser extent to Anatolia and were adapted, adjusted, and altered according to political, social, and economic circumstances. Early twentieth-century socialism not only arrived by various means, that is, through roving revolutionaries, workers, and print – all taking advantage of new technologies of communication and transportation, that is, railways, steamships, and telegraph – but it also came in many varieties, was often vaguely expressed, and commonly intersected with nationalist and even anarchist concepts. Therefore, our revolutionaries not only crossed physical boundaries, but they also traversed ideological ones through experimentation with popular global ideas that may be viewed either as eclecticism or synthesis. Armenian revolutionaries in Iran and the Caucasus ran the gamut from the minority social democrats to the socialist-nationalist Dashnaks and everything in-between like the Hnchaks. Moreover, within these groups, one could find a spectrum of ideological tendencies. What versions of socialism they espoused or what aspects of anarchism they found appealing was for the most part due to changing local, regional, and global circumstances and needs as well as their relationship with the national question. Familiarity with global ideologies like socialism and anarchism and ideas like decentralization and federalism came not only from reading but also involved face-to-face encounters, correspondence, and even collaboration between revolutionaries in Iran and the Caucasus on the one hand and European revolutionary thinkers on the other. They disseminated these ideas through their own translations, publications, and circulation of major socialist and anarchist theoreticians. Based on Dashnak archival documentation and Armenian-language contemporary periodicals and other publications in Europe, South Caucasus, Ottoman Empire, and Iran, this paper explores the crisscrossing of revolutionaries and the circulation and transformation of revolutionary ideas as they traversed across imperial frontiers in Eurasia.