The internal pressure of a vacuum interrupter (VI) is increased by arc heat, ceramic cracking, gas leakage, and manufacturing defects. Accordingly, the dielectric strength of VI rapidly decreases. To improve the reliability of power transmission, efficient maintenance through the real-time monitoring of the vacuum degree is essential. However, real-time monitoring of the vacuum degree is difficult, and related research is scarce. Additionally, due to the insulation problems of this technology, there are few commercially available products. Therefore, this paper proposes a method for real-time monitoring of the vacuum degree and an insulation supplement design for a distribution class VI. First, dielectric experiments were conducted to identify the section in which the dielectric strength of the VI rapidly decreased according to the vacuum degree. Second, for real-time monitoring of the VI, several factors were proposed through the partial discharge in the VI, while the capacitance characteristics of the VI were calculated to improve the signal of the internal partial discharge. Finally, to supplement the dielectric problems of the solid insulation high voltage apparatus that occur when real-time monitoring technology is applied, the insulation supplement design was performed through the finite element method (FEM).