In the last few decades, a growing number of theorists have suggested that the natural environment can be a platform for promoting cooperation between former adversaries and can perhaps contribute to peacebuilding. However, environmental cooperation has not lived up to these claims. In many cases, such cooperation has largely been ineffective and/or inequitable. Therefore, there is a growing awareness that we cannot be overly optimistic at the first signs of 'cooperation'. It is argued that this reality results from the great complexity inherent in cooperative interactions. This paper explores the nature of such cooperation in two Israeli-Palestinian case studies. The Israeli-Palestinian conflict is one of the longest-running protracted conflicts in the modern era and is currently characterised by a political stalemate. However, there is also a willingness by some at the local level to cooperate. Therefore Israel/Palestine provides an ideal case study. The findings of the paper illuminate the complex nature of environmental cooperation and reveal that even with the presence of good intentions, cooperation at the subnational level is impacted by the broader socio-political structures and contexts within which it is embedded. In these case studies, this is negatively affecting both the nature and scale of the processes and outcomes.Ultimately, these factors are making such interactions limited, unstable and/or prone to collapse. The paper concludes that only by conducting in-depth multitiered and context-specific analyses of cooperative processes and subsequently finding ways to overcome the identified barriers can we move towards more successful environmental cooperation.