The history of the Cold War has rarely been looked at through the eyes of the smaller powers, especially ones in the Balkans. Works have also often ignored the actual workings of the international socialist market, and the possibilities it created for some of these small countries. The conventional wisdom has also prevailed that the Eastern Bloc was irreversably lagging technologically, and its societies had failed to enter the information age after the 1970s, one among a myriad of reasons for the failure of socialism. Using the prism of a commodity history of the Bulgarian computer and an ethnography of the professional class that built it and worked with it, this dissertation argues that such narratives obscure the role of small states and the importance of technology to the socialist project. The backward Bulgarian economy exploited the international socialist division of labour and COMECON’s mechanisms to set itself up as the “Silicon Valley” of the Eastern Bloc, garnering huge profits for the economy. To do so, it did not hue a politically maverick road but exploited its political orthodoxy and Soviet alliance to the full, securing huge markets. Importantly, this work also shows that the state facilitated massive transfers of knowledge and technology through both legal and illicit means, using its state security and economic organisations to look to the West. This made the Iron Curtain much more porous for a growing cadre of technical intellectuals who were trusted by the regime in order to create the golden exports of the country. This transfer and mobility helped create an internationally plugged-in and fluent class of engineers and managers, at odds with most of the rest of the economy. At the same time, the Global South became an important area of exchange where these specialists competed with both nascent protectionist regimes and international firms. Using India as a case study, this dissertation shows how Bulgarian met the First World on the grounds of the Third and learned to market, negotiate, advertise, and service customers – a skillset that was then applied to its socialist dealings. Finally, the dissertation examines the domestic impact of such policies. The regime wished to use cybernetics and computing to solve the problems of its lagging economic growth, as well as usher in communism. It introduced both the widespread discourse of technological revolutions to its population, and robots and automation to some of its factories. This created both anxieties and hopes among workers, as well as vibrant philosophical debates about the future roles of humans in the information society, among both technical and humanistic intellectuals. Ultimately, however, the economic inefficiency undermined the promise and this failure was utilised by some technical managers to call for reforms, playing a hand in the end of the regime. They managed to negotiate the transfer to capitalism better than most, utilising their financial and business links, while thousands of engineers also found a better life than the vast majority of Bulgarian workers, through emigration or their possession of cutting edge skills. Using Bulgarian, Russian, Indian archives as well as interviews with living actors, the dissertation thus intervenes in both the view of the Iron Curtain as an impenetrable barrier for ideas, and 1989 as a convenient end point for communism’s legacies. It shows both the creation of new professional classes and how they were plugged into global developments, arguing that some people in the socialist bloc did enter the information age, and it is by paying attention to their actions and interests that we can get a better understanding of the developments of late socialism and its end.