Power electronic conversion systems introduce different types of voltage stresses on the high-voltage epoxy cast insulation in medium-frequency transformers (MFTs), which challenged the reliability of MFTs. The endurance of epoxy insulation at different voltage (AC, DC and pulse) and environmental (thermal and humidity) stresses was studied using encapsulated electrodes in the absence of partial discharge. To assess aging processes and select aging state indicators, various tests including AC breakdown strength (BDE), broadband dielectric spectroscopy (BDS), small-angle X-ray scattering (SAXS), Fourier-transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC) were at first conducted on aged flat samples. The increase of mesoscopic free volume from SAXS result and local densification (physical aging) of epoxy network from DSC result were both found. BDE is proved to be sensitive to various aging conditions, thus, determined as the test method for encapsulated samples. It is found that the physical aging effect under thermal stress at early aging stages can cause a reversible increase of BDE compared to non-aged samples. This effect can be erased by coupled medium-low electrical stress during aging. In contrast, a sufficiently high electric field will deepen the physical aging extent. Occasional sample failures were observed simultaneously within this process. According to SAXS and DSC results on flat samples, the failure of encapsulated samples is possibly attributed to the chain fracture around increased mesoscopic free volume during electron bombardment and microcracks generated by interfacial stress release during physical aging. At longer aging period, the volumetric absorption and diffusion of chemical reactant (oxygen, water) in epoxy network at high temperature determines the eventual decrease of BDE, which can be accelerated by electric field. The aging with different voltage types were gauged by the reduction of BDE compared to pure environmental stress. Bipolar pulse brings heavier aging effect than AC at the same RMS value. However, the DC component has opposite effects on BDE with and without thermal stress.