Abstract: An optimization strategy for high speed machining of hardened die/mold steel based on machining feature analysis was studied. It is a further extension of the previously presented study on the thermal mechanism of end milling and constant cutting force control. An objective function concerning machining cost and associated optimization algorithm based on machining time and cutting length calculation was proposed. Constraints to satisfy specific machining strategies when high speed machining the hardened die/mold steel, trochoid tool path pattern in slot end milling to avoid over-heat and feed rate adaptation to avoid over-load, were also discussed. As a case study, the tool selection problem when machining a die part with multiple machining features was investigated.