High speed machining (HSM), specifically end milling and ball end cutting, is attracting interest in the die/mold or aerospace industries for the machining of complex 3D surfaces. HSM of difficult-to-cut materials such as die/mold steels, titanium alloys or nickel based superalloys generates the concentrated thermal/frictional damage at the cutting edge of the tool and rapidly decreases the tool life. Following a brief introduction on HSM and reated aerospace or die/mold work, the paper reviews published data on the effect of cutter/workpiece orientation and cutting environments on tool performance. First, experimental work is detailed on the effect of cutter orientation on tool life, cutting forces, chip formation, specific force and workpiece surface roughness. Cutting was performed using 8 mm diameter PVD coated solid carbide cutters with the workpiece mounted at an angle of 45 degree from the cutter axis. A horizontal downwards cutting orientation proveded the best tool life with cut lengths ∼50% longer than for all other directions (horizontal upwards, vertical downwards, vertical upwards). Second, the cutting environments were investigated for dry, flood coolant, and compressed chilly air coolant cutting. The experiments were performed for various hardened materials and various coated tools. The results show that the cutting environment using compressed cilly air coolant provided better tool life than the flood coolant or the dry.