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A power transformer is expected to operate up to 40 years. With current cost-benefit calculations, the user is forced to perform maintenance that will bring a further extension of transformer life. The maintenance can only be based on on-site and off-site monitoring with extended analytical and electrical tests, which can define the service condition of the transformer and predict its further life expectancy. The life of a transformer is mainly dependent on the life of its solid insulation, and the life-limit is determined by the thermal degradation of the winding paper. The Kraft paper decreases in tensile strength with the progress of aging and, at some point, can no longer withstand the short circuit stresses. The monitoring of the complex permittivity of transformer oils, as a function of frequency and temperature, may provide information concerning the state of the insulation. In this article, we show the influence of air and oil type on the aging of pressboard under the influence of a considerable amount of moisture. The rate of the degree of polymerization, the development of furanic compounds, as well as the gas-in-oil analysis in comparison with the aging of the pure oil under the same conditions have been investigated.