Of the various chrono-stratigraphic entities of the Chalcolithic period in the southern Levant, the Middle Chalcolithic period (ca. 5300–4700 BCE) is the most poorly defined, with most of the relevant data coming from Tel Tsaf. While excavations at Tel Tsaf in the last two decades provide valuable information concerning the site’s upper occupational levels, the earlier strata and their material culture are still unknown. Past excavations focused on the later stage of the site’s occupation, leaving unanswered questions concerning the transition from the Early to the Middle Chalcolithic period. In order to shed new light on this topic, the current paper presents the results of the renewed research project, which focuses on the earliest occupational levels at Tel Tsaf, coinciding with the onset of the Middle Chalcolithic period. To start defining the characteristics of this episode, we present the archaeological layers, features, and finds uncovered just above the Lisan bedrock. We discuss the results’ implications and their contribution to an improved understanding of the Chalcolithic period’s broader temporal framework in the southern Levant.