Asymmetry is considered one of the most relevant features in today’s conflicts. In this article we address one particular type of asymmetry — structural asymmetry. After introducing the main characteristics and the different phases of these types of conflicts — i.e., conscientization, confrontation, negotiation, sustainable peace — we address the specificity of the Israeli-Palestinian case seen here as a typical case of a structurally asymmetric conflict. The aim is to explain why, despite the many negotiation phases this conflict has been through, none of them has ever led to a sustainable peace. On the contrary, each negotiation has brought on yet another confrontation phase, with a sort of never ending series of loops. The strong imbalance between the two sides, and the scarce reciprocal conflict awareness represent the two main reasons for explaining such a development.