This article examines the transnational ties between the Italian revolutionary left and Palestinian militants from the mid-1960s through the early 1980s. Some observers have cited these connections to explain the magnitude of Italian terrorism in the 1970s and early 1980s. However, in the absence of empirical research, the issue has remained murky. The archival sources and detailed interviews with protagonists used in the article shed light on this phenomenon by addressing four questions: first, the reception of the Palestinian cause within the Italian revolutionary left; second, the way Palestinian terrorist groups established roots in Italy and how the political context facilitated those efforts; third, the interactions between Italian and Palestinian militants both in Italy and in the Middle East; and fourth, the factors that strengthened or weakened the relationships between these entities. The evidence indicates that although Italian revolutionaries forged concrete ties with Palestinian militants and terrorists, these ties were not as extensively developed as some of the Italian leftists had hoped. The interactions encouraged radicalization but did not significantly foster violent escalation and terrorism in Italy.