Americans continue to investigate, deliberate, and wallow in the aftermath of Russia’s rebirth of “Active Measures” designed to defeat their adversaries through the “force of politics rather than the politics of force.” Kremlin interference in the 2016 U.S. presidential election represents not only the greatest “Active Measures” success in Russian history but the swiftest and most pervasive influence effort in world history. Never has a country, in such a short period of time, disrupted the international order through the use of information as quickly and with such sustained effect as Russia has in the last four years. Russia achieved this victory by investing in capabilities where its adversaries have vulnerabilities — cyberspace and social media. Putin’s greatest success through the employment of cyber-enabled “Active Measures” comes not from winning any single election but through the winning of sympathetic audiences around the world he can now push, pull, and cajole from within the borders of his adversaries. Much has been learned about Russia’s hackers and troll farms in the year since the 2016 presidential election, but there remain greater insights worth exploring from a strategic perspective when looking at the Kremlin’s pursuit of information warfare holistically.