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Basic decisions, such as judging a person as a friend or foe, involve categorizing novel stimuli. Recent work finds that people’s category judgments are guided by a small set of examples that are retrieved from memory at decision time. This limited and stochastic retrieval places limits on human performance for probabilistic classification decisions. In light of this capacity limitation, recent work finds that idealizing training items, such that the saliency of ambiguous cases is reduced, improves human performance on novel test items. One shortcoming of previous work in idealization is that category distributions were idealized in an ad hoc or heuristic fashion. In this contribution, we take a first principles approach to constructing idealized training sets. We apply a machine teaching procedure to a cognitive model that is either limited capacity (as humans are) or unlimited capacity (as most machine learning systems are). As predicted, we find that the machine teacher recommends idealized training sets. We also find that human learners perform best when training recommendations from the machine teacher are based on a limited-capacity model. As predicted, to the extent that the learning model used by the machine teacher conforms to the true nature of human learners, the recommendations of the machine teacher prove effective. Our results provide a normative basis (given capacity constraints) for idealization procedures and offer a novel selection procedure for models of human learning.