This paper explores the role of communications technology in the U.S.-Cuban relationship. It argues that the idea that anti-government dissidents will use the Internet, cell phones, and social media to foment a popular uprising on the island, modelled after the ‘Arab Spring’ is flawed because it fails to take into account the uniqueness of the Cuban situation. The paper then explores how it has become possible for this idea to have gained such traction in certain discourses in the United States. In doing so, the paper considers the history of paternalism and imperial hubris that has dominated U.S. policy toward Cuba, with an emphasis on the relationship during the Castro era. The paper demonstrates that current U.S. policy rests on fallacious assumptions about Cuba, the Cuban state and the relationship between the Cuban state and the Cuban people. The belief in a ‘Cuban Spring’ and in the idea that the United States could engender revolution in Cuba via communications technology is part of this larger narrative.