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One of the sub-branches of Central Semitic, Northwest Semitic, contains a number of languages with no established hierarchical relation among them: Ugaritic, Aramaic, Canaanite, Deir Alla, and Samalian. Over the years, scholars have attempted to establish a more accurate sub-branching for Northwest Semitic or to suggest a different genetic affiliation for some languages, usually Ugaritic. In this paper, we will argue that Aramaic and Canaanite share a direct ancestor, on the basis of a number of morphosyntactic features: the fs demonstrative *ðaˀt, the direct object marker *ˀayāt, the development of dative subjects with adjectival predicates, the use of the construct state with prepositions, the G imperfect inflection of geminate verbs, and the plural form of *bayt. We will also address arguments that Ugaritic is a Canaanite dialect, or that Canaanite and Ugaritic are more closely related. This proposal not only outlines a more coherent family tree for Northwest Semitic, but also accounts for numerous “Aramaic”-like features in some Canaanite dialects, primarily Biblical Hebrew, which have thus far been treated as the result of language contact in the early Iron Age.