Chapter 4 examines how anarchists handled the ramifications of the 1917 Russian Revolution. The revolution shaped the next decade and a half of anarchist agitation in the region as radicals attempted to figure out not only how to engage the new Communist state in Moscow, but also how to attract Marxists with whom anarchists worked and lived side by side. The post-1917 era also forced anarchists to confront the spread of US-backed anti-Communist surveillance. US intelligence agencies and their Caribbean partners tracked down and tried to suppress radicalism by expanding the Red Scare’s surveillance and repression into the Caribbean and targeting Caribbean anarchists who, from the heights of officialdom, were now seen as “Bolshevikis.”