The deterioration of the insulation in the windings of power transformers affects their lifespan. A commercial insulated Continuously Transposed Conductor (CTC) was studied experimentally, numerically and analytically. The purpose was to understand the mechanisms governing the mechanical failure of the insulating paper, and to achieve a criterion for predicting failure under different conditions. Samples of that insulated CTC were extracted from a coil and aged at 150 ᵒC for different durations inside vessels filled with naphthenic oil. Then the degree of polymerisation and tensile, compressive and shear mechanical properties of the insulation were measured/estimated. Aged insulated CTC samples were subjected to three-point bending tests, producing deformations compatible with a short circuit, and the fractures in the insulation were analysed. The bending test over a CTC sample was simulated by means of a FEM Program. The Norris failure model, applicable to a lamina, was adapted to the studied insulation materials. The predictions of that failure criterion agreed with experimental observations.