In this paper, we examine concepts and approaches explored in confederal proposals developed in the Kurdish and Palestinian contexts. Ideas about confederalism have been germinating in the Kurdish national movement for the last two decades and have resulted in a surprising experiment in the Syrian context, which permits for the first time an empirical investigation of these ideas. In the Israeli-Palestinian context, our evaluatio is limited to policy proposals for binational confederalism that have not yet resulted in concrete experiments. Despite these differences, however, we believe that comparing ideas about confederalism — as a vehicle for expressing national self-determination without the formal attributes of statehood — in these two disparate cases yields important insights. Both sets of proposals leave open important questions about how to connect potential (or actual) confederal projects to existing state structures or how, in practice, to transform state institutions in ways that make them more conducive to realizing confederal futures. On the other hand, there are also critical insights about the status of borders, citizenship, residency rights and democratic representation in both sets of proposals that reconfigure the relationship between political authority and territory in ways that are generative, precisely because they sidestep the methodological and conceptual binds of the nation-state. The paper makes a contribution to the literatures in comparative politics and comparative law that address decentralization, questions of constitutional design in divided societies, internal and external self-determination, and non-sovereign nations of the MENA region.