This work investigates the phonology of Tiberian Hebrew words ending on consonant clusters on the underlying level. This is achieved by first evaluating how these words were treated by traditional pre-generative grammars of Hebrew. This section of the study serves primarily to indicate the shortcomings in these explanations, and to indicate thereby the need for a generative study of these words. Thereafter the treatment of these words in terms of traditional generative phonology is discussed. In this section the explanations offered by two noted scholars in the field, Malone and Garr, are evaluated and compared. It is argued that these explanations are by far more adequate than the pre-generative explanations, but that they still miss some substantial linguistic generalisations. Finally, a proposal is offered for how these words can be treated in a non-linear approach to generative phonology. In this section the focus falls primarily on syllabification and how the site of vowel epenthesis is predicted by this process. The contribution of this study is twofold: On the one hand it offers the first detailed analysis of an aspect of the standard textbook “Tiberian Hebrew Phonology” of Malone (1993). On the other hand, it opens up the study of Tiberian Hebrew phonology to more recent developments in phonological theory.