This article examines the inflectional system of adjectives in Chaucer, Gower and Hoccleve, with particular reference to the adjectives ‘high’ and ‘sly’. Since these poets were careful metrists, scansion allows us to determine the syllabic status of adjectives in their verse. While in Chaucer and Gower, the grammatical system for the inflection of monosyllabic adjectives (final -e for weak and plural adjectives) is generally observed, there is good evidence to show that the system was breaking down in the case of ‘high’ and ‘sly’, which frequently appear without inflection in weak position. The article also shows that in Hoccleve's poetry inflectional -e had disappeared altogether in these adjectives, except at line ending. Editorial emendations that depend on this inflection are therefore incorrect. The explanation for the irregular behaviour of ‘high’ and ‘sly’ is probably related to the vulnerability of schwa after front vowels.