Accelerated aging tests have been extensively used on motor and generator insulation systems to simulate in a short time period the deterioration mechanisms occurring during normal operation of many years, to identify insulation system designs with longer life time and to support the qualification of a new system. The contribution presents results from extensive investigations on the behavior of two VPI machine test insulation systems (reference and candidate) with thermal class F (155 °C), which were subjected to three thermal overstresses in repeated cycles. After each thermal cycle the insulation system is subjected to mechanical stress, moisture, and voltage. In order to check the condition of the insulation systems in a non-destructive manner several properties of insulation like dissipation factor, insulation resistance and partial discharge quantities were measured after each thermal cycle. After that the end of life of the insulation systems were checked with ac voltage and impulse voltage. The results support the qualification by comparative evaluation and they indicate, how the changes in electrical and dielectric properties of insulation take place during the accelerated aging test.