This article examines the changing dynamics of censorship and social criticism in revolutionary Cuban cinema in order to make a case for studying allegory not as a mode whose meanings analysts should (or should not) reveal but, rather, as a contested social process. From the 1960s on, Cuban filmmakers turned to allegory as a means of resisting the reduction of art to propaganda and articulating more ambivalent takes on the Cuban Revolution. Yet spectators steeped in the political binaries of the Cold War often reduced films to arguments for or against socialism. Such paranoid readings have only grown more complex in the post-Soviet era, as changing strategies of state power, a growing orientation toward the global market, and the increasing availability of digital technologies enable more open criticism of the state in art and render criticism itself suspect. Drawing on this case study, this article argues that both depth models of interpretation and debates about “paranoid” or “symptomatic readings” fail to account for the social and political dynamics of texts. To understand how allegory and paranoid readings shape public debate and representation, we must examine how artists and audiences themselves mobilize the mode. This is especially true for Global South, state socialist, and authoritarian contexts, where traditions of political engagement through art, practices of skirting censorship through aesthetic indirection, and demands for depictions of the nation imposed by international art worlds foster practices of reading between the lines for hidden meanings in ways that sometimes cooperate with and sometimes work against artists’ aesthetic and political goals.