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The breakdown physics of transformer oil is investigated using high speed electrical and optical diagnostics. Experiments are done in self-breakdown mode utilizing a needle/plane geometry. Shadowgraphy combined with high-speed electrical diagnostics are aimed at measuring streamer expansion as a function of external pressure. Assuming a breakdown mechanism for negative needle based on bubble formation with subsequent carrier amplification in the gas phase implies a pressure dependence, which is observed in the experiments, i.e. the expansion velocity decreases with increasing pressure.