Over time, the Organization of American States has become institutionally and normatively more capable of defending democracy in the region. Yet the OAS is as selective in its interventions on behalf of democratic promotion today as it was in the early 1990s. To explain this puzzle, this study disaggregates democratic dilemmas according to issue areas, threats, and contingencies. It finds that the OAS responds more forcefully when the problem presents a clear and present danger both to the offending state and to other members. As threats become weaker or more ambiguous, the OAS tends to act more timidly, unless domestic constituencies cry out for its assistance or the United States puts its full weight behind the effort. Case study capsules provide empirical evidence to illustrate these arguments.