The thesis is grappling with the phenomena of Russia in modern Anglo-American history, especially as it relates to governance tensions concerning (digital) technology. Russia seems a paradox in Anglo-American circles: on the one hand, a serious security apparatus that threatens liberal capitalist democracies and the hearts/minds of world populations, on the other hand, a backward totalitarian regime vulnerable to foreign and/or popular reform. The central investigation follows two complementary lines of inquiry around this paradox. On the one hand, my work maps Anglo-American perspectives about Russia and shows how they often were built on incomplete understanding or even domestic projections. On the other hand, I draw on primary and secondary Russian-oriented sources to unpack the dense geographies – cultural, financial, legal, political, and social – that constitute this black box society, Russia. The thesis focuses on two historical periods in relation to three technological clusters: 1950s-1990s / cybernetics, 1990s-present / fintech (money laundering, anti-terrorist funding), and 2000s-present / cybersecurity (e.g., Facebook).