School-to-school collaboration has emerged as a key paradigm for fostering personal and institutional connections between Israeli and Diaspora youth, educators, and schools. Using the findings of a multi-year case study of a high school level twinning initiative, this article describes the challenges to this form of transnational collaboration and takes the first steps to articulating a theory of intervention of Israeli-Diaspora school twinning at the organizational level. The article suggests two processes, collaborative capacity and cultural competence, critical to development of positive and productive relationships in school partnerships. Institutional twinning is suggested as the goal of these interventions at the organizational level.