In experiments of machining hardened tool steels (such as AISI H11, H13, and D2, up to 56 HRC) by commercial Ø 0.5 mm square endmills, it is observed that the tested micro endmills showed severe wear at an early stage of the process due to chipping off around cutting edge corners, resulting in unsatisfactory tool life and product appearance (burr formation). Detailed examination of current tool geometry shows that it is mainly inherited from that of macro endmills, making the cutting edge corners the weakest part on the tool. As the micromilling process is characterized by small values of machining parameters, the cutting edge corners of the micro endmill are the most loaded part of the cutting edges. New design rules are studied for improving the stiffness and strength of micro endmills used in micro hard milling applications. Analytical modelling and finite element method analysis are used to aid the design of tool geometry. By using a larger neck angle, optimizing tool core geometry, and choosing a negative rake angle, tool stiffness and cutting edge strength are improved. The new endmill designs, both two-flute and four-flute, are tested in experiments on hardened tool steels and showed considerable lower tool wear and increased tool life. Furthermore, the geometrical accuracy and appearance of the workpiece (burr formation) has been improved drastically.