In the Italian peninsula, the Late Middle Paleolithic exhibits significant technological diversity, featuring blades, points, and bladelets. Assemblages displaying these distinctive characteristics have, in some cases, been labeled as Musteriano evoluto or Evolved Mousterian, and they are interpreted as contributing to the technological and typological variability within the Middle Paleolithic. In this study, we report the results of a detailed technological analysis of the lithics recovered from the latest layers preserved at Riparo l’Oscurusciuto (SU1 to SU3) in southern Italy. These layers were previously attributed to the Late Mousterian based on their chronological age and a preliminary techno/typological analysis of a small number of artifacts. Our comprehensive analysis of entire assemblages reveals the presence of original technological features, including blades, bladelets, and specific production of micro-points on flake cores. Some of these technological traits are comparable to those recently described at Grotte Mandrin in south-eastern France, which have been attributed to an early phase of the Initial Upper Paleolithic and associated with one modern human tooth. The study confirms the variability of the Late Middle Paleolithic in southern Italy and emphasizes the necessity to reassess it considering recent theories on the earlier arrival of Homo sapiens in Europe and their potential interaction with local populations.