The paper proposes a classification of adaptive materials and coatings for tool purposes, showing the ability to adapt to external heat and power influences, thereby improving tool life. Creating a cutting tool made of composite powder high speed steels containing refractory TiC, TiCN, and Al2O3 compounds for milling 41CrS4 steel demonstrated the effectiveness of the adaptive materials. The tool material characteristics under the external loads’ influence and the surface layer adaptation to the heat–power exposure conditions were shown by the temperature field study using a semiartificial microthermocouple method (the level of fields is reduced by 20%–25% for 80% HSS + 20% TiCN), frictional interaction high-temperature tribometry (the coefficient of friction did not exceed 0.45 for 80% HSS + 20% TiCN at +20 and 600 °C), laboratory performance tests, and spectrometry of the surface layer secondary structures. Spectral analysis shows the highest spectrum intensity of TiC2 after 5 min of running in. After 20 min of milling (V = 82 m/min, f = 0.15 mm/tooth), dicarbide decomposes and transits to thermally stable secondary phase films of good lubricity such as TiO (maximum) and TiN (partially). There was an increase in tool life of up to 2 times (>35 min for 80% HSS + 20% TiCN), and a decrease in the roughness of up to 2.9 times (Ra less than 4.5 µm after 25 min of milling).