One hundred fifty years since the first published reference in modern western scholarship to ancient wine production in the Negev Highland desert, much is known about its hydrological, climatic, agricultural, economic, social, and political context. Yet, in 2020 two studies reached opposite conclusions regarding the extent and intensity of Negev Highland viticulture, its relationship to Byzantine ‘Gaza wine’ and the associated regional wine trade. This raises wider questions on how to evaluate apparently conflicting archaeological evidence for ancient microregional production and trade, with relevance to longstanding debates on the nature of the ancient Mediterranean economy and the onset of the Medieval period in Europe. We survey previous research on Negev Highland viticulture, including the two most recent papers, demonstrating problems of equifinality in the calculations-based approach to ancient production/consumption, and clarifying our own position regarding the relationship between archaeologically attested Negev viticulture and 'Gaza wine’ of Late Antique historical texts. We then analyse additional sources of new evidence contributing to a more holistic synthesis of Negev Highland wine production and trade. At this sesquicentennial commemoration of Negev viticulture’s historiography, we close with unresolved issues and promising directions for future research.