Since the fall of the Soviet Union, Russia has been unprecedented in its embrace of modern technology for the execution of its foreign policy and intelligence operation. This article examines Russia’s relationship to the internet and computer technology, beginning with the early 1990s and detailing the growth of technology’s popularity with the Russian public and Russian government up through 2017. Particular attention is paid to the skill with which Russia’s illiberal political institutions and security services exploit the ‘wild west’ nature of the internet and the manipulable nature of modern technology and media, as well as how and why the West and U.S. failed to anticipate Russia’s rise as a digital superpower and continue to fail to counter its dominance.