Using the developed method, the deformation regularities of artificial cone-shaped defects’ models on wire rod and wire during their multiple drawing are experimentally determined for the first time. As found, for the most part, the smoothing of such defects occurs more intensively, the greater the total wire elongation and the initial values of the depth and width of the defects. These data are compared with the results of the previous similar investigations on wire deformation in the presence of defects of predominantly transverse orientation and predominantly longitudinal one relative to the drawing axis. As shown, the qualitatively obtained new results are closer to the ‘transverse’ defects’ deformation patterns, and the quantitative differences can be explained by the presence of a volumetric scheme of the metal stress–strain state around the artificial surface violation of its continuity. The influence of the presence of such artificial formations (‘defects’) on the condition of uninterrupted wire drawing is determined. Attention is paid to the possible additional negative influence of ‘defects’ as stress concentrators on the stability of the drawing process. The results of the investigation may be useful in designing the routes for continuous multiple drawing of a work-piece with the probable presence of continuity defects on it, and in investigating the mechanism of deformation of such surface defects to obtain drawn wire of acceptable quality. A promising direction of research is to combine the data of existing work with known methods for calculating force conditions of deformation and thoroughly quantifying the parameters of designed routes for multiple stable wire drawing.