In this paper, machinability of AISI 316 austenitic stainless steel was investigated using cryogenically treated and untreated high-speed steel (HSS) twist drills. Machinability of AISI 316 austenitic stainless steel was evaluated in terms of thrust force, tool life, surface roughness, and hole quality of the drilled holes. Experimental results showed from 14% to 218% improvements for treated tool lives. Thrust force, surface roughness, and hole quality are better with treated drills when compared with untreated drills. These improvements were mainly attributed to formation of fine and homogeneous carbide particles and transformation of retained austenite to martensite. Microhardness and microstructure observations verified these formations.