Cross-linguistic generalizations about grammatical contexts favoring syncretism often have an implicational form. This paper shows that this is expected if (i) morphological paradigms are required to be both as small and as unambiguous as possible, (ii) languages may prioritize these requirements differently, and (iii) probability distributions for grammatical features interacting in syncretic patterns are fixed across languages. More specifically, this approach predicts that grammatical contexts that are less probable or more informative about a target grammatical feature $ T $ should favor syncretism of $ T $ cross-linguistically. The paper provides evidence for these predictions based on four detailed case studies involving well-known patterns of contextual syncretism (gender syncretism based on number, gender syncretism based on person, aspect syncretism based on tense, and case syncretism based on animacy).