Operating experience has shown that vibration can cause pressure fluctuations and initiate bubbles at the oil gap, which seriously threatens the insulation properties of oil-immersed power equipment. The main aim of this study was to determine the characteristics and mechanism of bubble initiation at the transformer oil gap under vibration in this paper. The results show the existence of the vibration-dependent bubbling phenomenon at the oil gap. Interestingly, bubbles initiate during the process of gap expansion, and the evolution of bubble morphology was further analyzed. The threshold characteristic of the bubble initiation process was found, and the relevant influencing factors were experimentally obtained. In the range considered in this study, higher gas content, higher temperature, and lower moisture content are conducive to bubble initiation at the oil gap under vibration, while vibrational frequency does not affect the threshold characteristic of bubble initiation process. The vibration-dependent bubbling phenomenon can be attributed to the vibration-induced cavitation process caused by the decrease in pressure at the oil gap. The influence mechanism of the above factors on the threshold characteristics of bubble initiation was further discussed. This study contributes to providing a reference for risk assessment of abnormal vibration of oil-immersed power equipment.