As the voltage levels of solid-state transformers (SSTs) increase using medium-voltage switches, high-frequency transformers (HFTs) used inside SSTs are subjected to increased electrical stress. This stress, characterized by high voltage, high-frequency pulsewidth modulation (PWM) voltage, can cause insulation partial discharge (PD) and potentially lead to failure of the HFT insulation system. While PD behavior under power-frequency sinusoidal voltage has been extensively studied, the behavior of HFT insulation under PWM square pulse conditions is less well understood. To address this gap, a high voltage high-frequency PWM voltage PD test platform is developed and high-frequency current transformer (HFCT) and ultra-high-frequency (UHF) antenna are used for PD signal detection. PD tests are performed under a variety of PWM conditions including PWM frequency, rise time, voltage amplitude, and different insulation layers to thoroughly investigate the HFT insulation behavior. The PD characteristics of repetitive PD inception voltage and phase-resolved PD patterns at different PWM conditions are recorded and analyzed under PWM conditions. In addition, this article explores the underlying PD mechanisms of the HFT insulation under high-frequency PWM stress, providing insights to explain the observed test results. The findings from this research provide essential references and lay a solid foundation for future advances in optimal design, health monitoring, reliability analysis, and lifetime prediction for HFTs in power electronics applications.