This essay explores three historical events that took place during the nineteenth, twentieth and twenty-first centuries in Puerto Rico to extract the ways in which new technologies became the vehicle for massive political and economic disruptions. The first event recalls the electrification of Old San Juan and the change from kerosene gas to electricity, which prompted a grassroots revolt in which the quarter’s street-lamps were torn down. The second was less a mass revolt than a symbolically resonant moment in the encounter between the Puerto Rican independence movement and the Puerto Rican establishment when militants from a pro-independence faction, allegedly planning on destroying the Communication Towers at Cerro Maravilla in 1978, were raided by the police, resulting in the deaths of two young activists. The last historical occurrence concerns the Internet response to the budget crisis that forced the government of Puerto Rico to shut down in 2006. In conclusion, I use the patterns I uncover in these events as a vector into understanding colonialism as one of the key determinants of the zone of encounter between technological change and popular opinion in Puerto Rico, both under the Spanish and under the rule of the United States.