Why do people change their strategies for solving problems? In this research, we tested whether negative feedback and the context in which learners encounter a strategy influence their likelihood of adopting that strategy. In particular, we examined whether strategy adoption varied when learners were exposed to a target strategy in isolation, in conjunction with their own current strategy, and in conjunction with another novel strategy. We also investigated the roles of individual differences, including learners’ need for cognition and their confidence in their current strategies. In Study 1, undergraduate participants who encountered a target strategy in isolation were more likely to adopt it than participants who encountered it in the context of their own current strategy. Negative feedback, low confidence, and high need for cognition also predicted greater adoption. In Study 2, we examined whether rates of strategy adoption depended on the target strategy itself. Indeed, participants were more likely to adopt one strategy than the other, and the effects of feedback also varied across strategies. Individual differences— need for cognition and confidence— also influenced patterns of strategy adoption. These results suggest that strategy adoption depends on the confluence of many factors, including the context in which a target strategy is introduced, characteristics of the learner, and characteristics of the strategy itself.