To examine the political factors that influence the use of legal mechanisms to resolve territorial disputes, we model the decision to pursue arbitration and adjudication as part of a bargaining process in the shadow of war. We find that arbitration and adjudication can help prevent bargaining breakdown, but states only pursue and comply with such measures when the expected ruling reflects the balance of power between them. To test the theory, we examine compliance with arbitral and adjudicated rulings on territorial claims. In line with our expectations, states are less likely to comply when the stronger disputant is asked to make greater concessions. We conclude that power politics constrains the conditions under which legal mechanisms can be used to successfully manage contentious claims over territory.