Learning from negative outcomes is of fundamental interest to scholars. Yet most research in this area explores learning from actual outcomes. By contrast, we add to the literature by setting forth a theoretical framework that highlights learning from the anticipation of negative outcomes rather than actual outcomes. Using an inductive, multiple case research design, we develop an emergent typology for how anticipatory learning occurs. We show how each type of anticipatory learning is triggered and uniquely influences search and solutions. We also detail how anticipatory learning is similar to, but different than, learning from actual negative outcomes. A central contribution of this study is setting forth anticipatory learning as a primary form (versus a special case) of learning in most organizations. We conclude by identifying implications for organization theory and strategy.