Motivation affects the degree to which people engage in tasks as well as the processes that they bring to bear. We explore the proposal that a fit between a person’s situationally induced self-regulatory focus and the reward structure of the task that they are pursuing supports greater flexibility in processing than does a mismatch between regulatory focus and reward structure. In two experiments, we prime regulatory focus and manipulate task reward structure. Our participants perform a rule-based learning task whose solution requires flexible strategy testing as well as an information-integration task for which flexible strategy use hinders learning. Across two experiments, we predict and obtain a three-way interaction between regulatory focus, reward structure, and task. Relative to a mismatch, a match leads to better rule-based task performance, but worse performance on the information-integration task. We relate these findings to other work on motivation and choking under pressure.