This paper describes a comparison of overvoltage propagation in transformer windings. Expanding and evolving electrical networks comprise various classes of transient waveforms, related to network reconfigurations, failure stages and switching phenomena, including new sources based on power electronics devices. In particular, the integration of renewable energy sources—mainly solar and wind—as well as expanding charging and energy storage infrastructure for electric cars in smart cities results in network flexibility manifested by switching phenomena and transients propagation, both impulse and oscillating. Those external transients, having a magnitude below the applied protection level may have still a considerable effect on winding electrical insulation in transformers, mainly due to internal resonance phenomena, which have been the root cause of many transformer failures. Such cases might occur if the frequency content of the incoming waveform matches the resonance zones of the winding frequency characteristic. Due to this coincidence, the measurements were performed both in time and frequency domain, applying various classes of transients, representing impulse, chopped (time to chopping from 1 µs to 50 µs) and oscillating overvoltages. An additional novelty was a superposition of a full lighting impulse with an oscillating component in the form of a modulated wavelet. The comparison of propagation of those waveforms along the winding length as well as a transfer case between high and low voltage windings were analyzed. The presented mapping of overvoltage prone zones along the winding length can contribute to transformer design optimization, development of novel diagnostic methodology, improved protection concepts and the proper design of modern networks.