Thermal modeling and temperature assessment of electrical machines often rely on the use of lumped-parameter thermal networks. A historic limitation of analytical thermal models is their need for an experimental fine-tuning, necessary for selecting the appropriate values of thermal conductivity and convection heat transfer coefficients. This evaluation procedure is commonly carried out at the design stage of a new machine, by assuming that its thermal behavior will remain unchanged throughout its whole lifetime. This paper demonstrates, through an in-depth experimental investigation, how the capability of heat extraction from a machine's hot spot towards the coolant can be strongly affected by the level of thermal aging of its insulation system. Based on the experimental findings, a decrement of the winding equivalent thermal conductivity is noted as the thermal aging accumulates, with a corresponding progressive increment in hot-spot temperature.