The trend in die/mold manufacturing at present is towards the hard machining at high speed to replace the electron discharge machining. Failure forms of the AlTiN-coated micro-grain carbide endmill when used for the machining of JIS SKD61 (HRC 53), a widely used material in die/mold manufacturing, are investigated. The endmill shows a characteristic that tool life decreases greatly due to the chipping when overload occurs or the rapid increase of wear when over-heat accumulation in cutting edges. As a consequence of the investigation, a strategy to regulate heat generation in the end milling process is proposed. This is accomplished by controlling the cutting arc length, i.e. the length of each flute engaging workpiece in a cutting cycle. Case studies on the slot end milling and comer rounding are conducted. The results show that the proposed strategy suggests the optimal tool path as well as the optimal pitch between successive tool paths under the cutting time criterion.