In this article, the impact of the waveform switching frequency (SWF), overshoot (OS), and rise time on the time-to-failure and the endurance of Type II machine insulation is investigated. Reference life curves at 1 and 4 kHz SWF are derived utilizing a unipolar repetitive square-impulse of 15% OS and 300 ns rise time. The effects of the impulse OS and rise time in the ranges of 0%–30% and 400–600 ns are also evaluated and reflected on the established reference life curves. Based on the endurance test results and the reported time-to-failure data, it is evident that the turn insulation is subjected to additional stress factors when energized by an inverter supply as opposed to the stresses exhibited by sinusoidal waves. This indicates an incomparable aging rate between the two types of waveforms, even at similar peak voltages applied, resulting in inadequate use of sinusoidal supply to qualify inverter-fed machines. Moreover, the OS component of the waveform is found to have a substantial impact on the endurance of turn insulation apart from the jump voltage impact, and therefore, is identified as a significant factor influencing the life of turn insulation independent of other factors. Moreover, the reported results of the time-to-failure analysis advocate a nonlinear relationship between the SWF and the life of turn insulation, whereas the waveform rise time is found to have a negligible impact within the considered range in this study.