Digital propaganda of the Russian government seeks to insulate Putin’s leadership from any domestic challengers and aid in his foreign policy ventures, which increasingly sets Russian interests off against the West. Yet the propaganda tools, including trolls and bots, were conceived and perfected in the pockets of political competition and a globally integrated market economy still left in Putin’s Russia. I discuss how the vibrant Russian blogosphere, left unattended by the government and laser-focused on taking over the traditional media, created the demand for sophisticated online propaganda and censorship tools. I also discuss how the advanced Russian online media and tech sector helped to meet this demand. I conclude with a preliminary report on the detection and exposure of government propaganda online, which could be applicable beyond Russia.