Thermal, electrical and mechanical stresses age the electrical insulation systems of high voltage (HV) apparatuses until the breakdown. The monitoring of the partial discharges (PDs) effectively assesses the insulation condition. PDs are both the symptoms and the causes of insulation aging and—in the long term—can lead to a breakdown, with a burdensome economic loss. This paper proposes the convolutional neural networks (CNNs) to investigate and analyze the aging process of enameled wires, thus predicting the life status of the insulation systems. The CNNs training does not require any kind of assumption of how the factors (e.g., voltage, frequency and temperature) contribute to the life model. The experiments confirm that the proposal obtains better estimations of the life status of twisted pair specimens concerning existing solutions, which are based on strong hypotheses about the life model dependency on the factors.