Background/Aims: Lexically guided perceptual learning in speech is the updating of linguistic categories based on novel input disambiguated by the structure provided in a recognized lexical item. We test the range of variation that allows for perceptual learning by presenting listeners with items that vary from subtle within-category variation to fully remapped cross-category variation. Methods: Experiment 1 uses a lexically guided perceptual learning paradigm with words containing noncanonical /s/ realizations from s/ʃ continua that correspond to “typical,” “ambiguous,” “atypical,” and “remapped” steps. Perceptual learning is tested in an s/ʃ categorization task. Experiment 2 addresses listener sensitivity to variation in the exposure items using AX discrimination tasks. Results: Listeners in experiment 1 showed perceptual learning with the maximally ambiguous tokens. Performance of listeners in experiment 2 suggests that tokens which showed the most perceptual learning were not perceptually salient on their own. Conclusion: These results demonstrate that perceptual learning is enhanced with maximally ambiguous stimuli. Excessively atypical pronunciations show attenuated perceptual learning, while typical pronunciations show no evidence for perceptual learning. AX discrimination illustrates that the maximally ambiguous stimuli are not perceptually unique. Together, these results suggest that perceptual learning relies on an interplay between confidence in phonetic and lexical predictions and category typicality.