Paraguay is often overlooked in studies of Latin American guerrilla movements during the Cold War. There are two main reasons for this: the magnitude of the repression exercised by military regimes, especially in the Southern Cone, and particularly the magnitude of the counter-insurgency practices of Alfredo Stroessner’s dictatorship, as revealed by the discovery of documents in the so-called Archives of Terror. The purpose of this chapter is therefore to contribute to the knowledge of Paraguayan revolutionary initiatives during the 1950s and 1960s based on three organisations: 14th of May Movement, United Front for National Liberation (FULNA) and Political-Military Organisation (OPM). The failure of all their revolutionary strategies reveals the counter-insurgency capacity of the Paraguayan dictatorship, decisively included in transnational planning under the name of Operation Condor.