With the increased interest in alternative digital media in contemporary Cuba, scholars tend to overlook the fact that alternative media have a long and complex history that well precedes the so-called “digital revolution.” In adopting a broader, historical focus to analyze four convulsive periods of Cuba’s history in which technological affordances have enabled alternative communication to emerge, this chapter reconstructs radical media experiences during the Ten Years’ War, The Cuban War of Independence, and the dictatorships of Gerardo Machado and Fulgencio Batista. It draws from the concept of Downing’s (2001) radical media and Rodríguez’s (2001) citizen media. The chapter offers an overview of the most important alternative media and their objectives and links to revolutionary movements. Media content, internal organization, use of technology, means of distribution, and the repercussions they faced are explored. It then proposes five traits that tie the different eras together with respect to contemporary alternative communication: illegality and repression, use of new technology, innovative means of production and distribution, professional expertise, and the intervention of diasporic communities. The chapter argues that alternative communication in Cuba has been a continuous historical, sociopolitical phenomenon, rather than an exceptional, ahistorical phenomenon merely afforded by today’s spread of digitalization.