The article presents an analytical review of methods for cutting process on-line monitoring that are applicable for enhancing the performance of technological production systems and experimental verification of some findings of the analytical research. The interrelation between the thermophysical properties of the “tool-workpiece” contact pair and the technological processing conditions along with the cutting operation outcome has been considered. The degree of influence certain factors and the cutting conditions have on the machined surface roughness parameters and the cutting forces components have been analyzed. The analysis results showed the possibility of on-line estimating of the machined surface microrelief of with the application of dynamometric methods for assessing the cutting force vibration in order to increase the assurance reliability of the required quality parameters. There are mathematical models that enable us to reliably predict the values of the surface average roughness and the cutting forces radial and axial components.