International rivers create complex relationships between their riparian states, which can contribute to economic, political, and social losses. Treaties provide a means for states to coordinate their actions in managing international river disputes to minimize these losses. However, there is little knowledge about treaty content and the factors influencing treaty design. We test whether a relationship exists between the challenges of negotiating, complying, and distributing the gains in bilateral, multilateral, and basin-wide negotiation contexts and the depth of cooperation along with the degree of institutionalization. While the great challenges confronting multilateral or basin-wide negotiations can produce treaties that focus on joint gains and shallow cooperation to secure the signature of riparians, we find that they can also provide opportunities for deeper, more behavior-altering, cooperation. To manage the difficulties of maintaining multilateral cooperation, we find a higher degree of institutionalization. We also find that bilateral negotiations provide states with opportunities for deeper cooperation, but a lower degree of institutionalization.