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It is important to investigate electrostatic charging phenomena in insulating oil pressboard (PB) composite system in electrical insulation design of oil-immersed power transformers. Our research aim was to clarify the charge accumulation mechanism at the oil/PB interface under static and flowing oil. In this paper, we directly measured the time variation of the electric field in the insulation system using a Kerr electro-optic technique. Results show the time decaying characteristics of an electric field in oil by charge accumulation. The results are influenced by oil flow conditions. Based on the measurement results, we propose a theoretical model for charge accumulation to clarify the process quantitatively. In the model we took the oil volume contributing to the charge accumulation into account, and analyzed the charge behavior. Finally, we clarified the charge accumulation mechanism at the oil/PB interface under oil flow conditions both with and without charging.