Metals such as Cu, Al, Ni, Ta and stainless steels, despite their softness and ductility, are considered difficult to machine. This is due to large cutting forces and corresponding formation of a very thick chip during cutting and hence these metals are referred to as “gummy”. Their poor machinability of these materials arises because of an unsteady and highly redundant mode of plastic deformation referred to as sinuous flow. The prevailing plastic deformation mode during machining can be overcome by the application of certain coatings and chemical media on the un-deformed free surface of the workpiece ahead of the cutting process. Using in-situ imaging and concurrent force measurements we present two different mechanochemical routes through which these media can improve machinability. The first route, which requires chemicals that adhere to the metal surface, such as glues and inks, improves cutting by inducing a change in the local plastic deformation mode — from sinuous flow to one characterized by periodic fracture or segmented flow. The second route, which requires chemicals that can react with the workpiece to form a low-friction layer, changes the sinuous flow mode to a smooth, laminar one. Both routes decrease cutting forces by more than 50% with order of magnitude improvement in surface texture as characterized by measured roughness and defect density. The results suggest a broad range of opportunities for improving performance of machining processes for many difficult-to-cut gummy metals.