Tool wear is one of the critical issues which deteriorate machining accuracy in ultraprecision machining. However, tool setting errors caused by the change of worn tool during a machining operation should be carefully compensated by identifying the gaps between the ideal tool center point and the actual tool center point, which inevitably lead to low machining efficiency. Because of the long consumption time of actual tool center point detection, this study aims at achieving on-machine shaping of a diamond tool which is commonly used in ultraprecision machining. In the previous study, shaping conditions without tool chipping are investigated by using various shaping materials. Then, in order to create a flank face that is necessary to realize preferable cutting, a pin gauge made of cemented carbide is adopted as the shaper. From the conducted experiments, it is found that the proposed on-machine shaping can create a specific cutting edge and a flank face on an ultraprecision machine tool.