Vacuum circuit breakers are increasingly used as switching apparatus in electric power systems. The vacuum circuit breakers (VCBs) have very good operating properties. VCBs are characterized by specific physical phenomena that affect overvoltage exposure of the insulation systems of other devices. The most important phenomena are the ability to chop the current before the natural zero crossing, the ability to switch off high-frequency currents, and the rapid increase in dielectric strength recovery. One of the devices connected directly to vacuum circuit breakers is the distribution transformer. Overvoltages generated in electrical systems during switching off the transformers are a source of internal overvoltages in the windings. The analysis of the exposure of transformers operating in electrical networks equipped with vacuum circuit breakers is of great importance because of the impact on the insulation systems of switching overvoltages (SO). These types of overvoltages can be characterized by high maximum values and atypical waveforms, depending on the phenomena in the circuit breaker chambers, system configuration, parameters of electrical devices, and overvoltage protection. Overvoltages that stress the internal insulation systems are the result of the windings response to overvoltages at transformer terminals. This article presents an analysis of overvoltages that stress the transformer insulation systems, which occur while switching off transformers in systems with vacuum circuit breakers. The analysis was based on the results of laboratory measurements of switching overvoltages at transformer terminals and inside the winding, in a model medium-voltage electrical network with a vacuum circuit breaker.