The Eneolithic era is represented by the highest level of technology for the making of stone tools. This is most clearly manifested in the cultures of the forest belt. The history of studying the forest-steppe and steppe spaces of the Volga region is shorter. Therefore, the source base for studying the characteristic and unique features of stone industries is less representative. Thus, over the last quarter of a century, only two sites containing materials from the period of interest have been studied in the Middle Posurye. This does not contribute to a final solution to a whole range of issues. One of the most complex is the aspect associated with the interpretation of the stone inventory of the Khvalynsk Eneolithic culture. If the belonging of tools made on large blanks to it does not cause lively debates among specialists, then the presence of microliths remains debatable. Their attribution to the Mesolithic period was not excluded. To develop this issue, the authors analyzed all available artifacts at the main Eneolithic sites on the border of forest-steppe and forest. The raw materials for the making of various categories of tools, their typological and metric indicators were taken into account. A comparison was made with the Mesolithic complexes of this region. In order to consider this issue on a broad territorial background, an analysis of the stone inventory of the Khvalynsk sites of both the semi-desert Northern Caspian and the steppe Volga region was carried out. The inserts were compared with similar products in the foreststeppe Volga region, Mariupol antiquities and materials of the Shibir type of Mangyshlak. As a result, the authors came to the conclusion that the inserts belonged to the Eneolithic industries both in the Middle Posurye and on a larger territory.