Categorization involves organizing perceptual information so as to maximize differences along dimensions that predict class membership while minimizing differences along dimensions that do not. In the current experiment, we investigated how neural representations reflecting learned category structure vary according to generalization demands. We asked male and female human participants to switch between two rules when determining whether stimuli should be considered members of a single known category. When categorizing according to the "strict" rule, participants were required to limit generalization to make fine-grained distinctions between stimuli and the category prototype. When categorizing according to the "lax" rule, participants were required to generalize category knowledge to highly atypical category members. As expected, frontoparietal regions were primarily sensitive to decisional demands (i.e., the distance of each stimulus from the active category boundary), whereas occipitotemporal representations were primarily sensitive to stimulus typicality (i.e., the similarity between each exemplar and the category prototype). Interestingly, occipitotemporal representations of stimulus typicality differed between rules. While decoding models were able to predict unseen data when trained and tested on the same rule, they were unable to do so when trained and tested on different rules. We additionally found that the discriminability of the multivariate signal negatively covaried with distance from the active category boundary. Thus, whereas many accounts of occipitotemporal cortex emphasize its important role in transforming visual information to accentuate learned category structure, our results highlight the flexible nature of these representations with regards to transient decisional demands.SIGNIFICANCE STATEMENT Occipitotemporal representations are known to reflect category structure and are often assumed to be largely invariant with regards to transient decisional demands. We found that representations of equivalent stimuli differed between strict and lax generalization rules, and that the discriminability of these representations increased as distance from abstract category boundaries decreased. Our results therefore indicate that occipitotemporal representations are flexibly modulated by abstract decisional factors.