This paper suggests a series of schemas aimed at eliminating the main drawbacks of existing schemas of Yiddish proto-vowels. It attempts to complete the schemas developed by other scholars mainly in two aspects, proposing derivational rules that (1) account for Proto-Western Yiddish and its sub-dialects and (2) explain the relation between the vowels of the German donor language and Yiddish proto-vowels. This analysis shows the impossibility of constructing a schema of a single Proto-Yiddish as a historical reality and thus implies the polygenesis of the system of stressed vowels and diphthongs of Yiddish. Proto-Western Yiddish and Proto-Eastern Yiddish had no common, specifically Jewish ancestor. The comparative analysis of various German dialects and Yiddish proposed here provides the basis for determining the regions (East Franconia and Bohemia, respectively) where the stressed vocalism of the Yiddish dialects likely appeared and the corresponding time period (the 14th–15th centuries).