The aim was to develop a methodology for monitoring the dynamic state of the links “machine tool – device – cutting tool – detail” comprising a cutting technological system as applied to turning specialized stainless steels using replaceable standard hardmetal inserts. The research object was the hard-to-treat non-corrosive stainless steels 09Х17Н7Ю, 12Х18Н10Т and 13Х15Н5 АМ-3. Monitoring was carried out by simulating plate coatings in the Deform software environment. The diagnostic criterion was the tool life period up to the wear level of 0.5 mm along the rear edge. The effect of coatings on the tool life period was assessed according to the following parameters: temperature in the cutting zone, tension in the tool material and tool deformation. As a result, 10 optimal coatings having the greatest impact on the state of the cutting technological system under study were selected. These coatings can be used for diagnosing the state of cutting technological systems. The coatings were distinguished in terms of architecture (design, composition,structure and coating method). A technique for monitoring and managing the state of cutting technological systems according to the results of diagnostics was proposed. The deviation of the revealed state of the cutting technological system from the desired state was estimated by the life period of tools with different coatings for the same time of their operation. The state of the system under study was considered effective provided that the maximum tool life period due to the use of an optimal coating was achieved. A technique allowing assessment of the state of technological cutting systems by their simulation according to the parameters “temperature in the cutting zone”, “tension in the tool material” and “tool deformation” was proposed. This technique also permits monitoring of the state of cutting systems by the parameter "tool life period" and managing their state according to the results of diagnostics through the use of the most optimal plate coatings. The developed technique can be used to reveal the optimal parameters of the cutting mode of hard-to-treat specialized corrosion-resistant steels.