This paper extends scholarship on multi-stakeholder initiatives (MSIs) in the context of corporate social responsibility in three ways. First, I outline a framework to analyze the strength of couplings between actors participating in MSIs. Characterizing an MSI as consisting of numerous local networks that are embedded in a wider global network, I argue that tighter couplings (within local networks) and looser couplings (between local networks) coexist. Second, I suggest that this coexistence of couplings enables MSIs to generate policy outcomes which address the conditions of a transnational regulatory context. I argue that MSIs’ way of organizing enables them to cope with three challenges: the stability, flexibility, and legitimacy of governance. Reflecting on these challenges, the article identifies a number of problems related to MSIs’ role in transnational governance. Third, I discuss the UN Global Compact as an illustrative case and examine problems and opportunities related to its stability, flexibility, and legitimacy.