The paper considers the problem of a wireless communication system’s physical level security for a multipath signal propagation channel and the presence of a wiretap channel. To generalize the propagation effects, the Beaulieu-Xie shadowed channel model was assumed. To describe the security of the information transfer process, such a metric as the secure outage probability of was considered. An analytical expression of the secure outage probability was obtained and analyzed depending on the characteristics of the channel and the communication system: the average value of the signal-to-noise ratio in the main channel and the wiretap channel, the effective path-loss exponent, the relative distance between the legitimate receiver and the wiretap and the threshold bandwidth, normalized to the bandwidth of a smooth Gaussian channel. The analysis considers the sets of parameters that cover all practically important scenarios for the functioning of a wireless communication systems: both deep fading (corresponding to the hyper-Rayleigh scenario) and small fading, both in the case of a significant line-of-sight component and a significant number of multipath clusters, and with significant shadowing of the dominant component and a small number of multipath waves, as well as all intermediate options. It is found out that the value of the energy requirements for guaranteed secure communication at a given speed is determined primarily by the power of multipath components, as well as the existence of an irreducible secure outage probability of a communication session with an increase for channels with strong overall shadowing of the signal components, which from a practical point of view is important to take into account when imposing requirements for the values of the signal-to-noise ratio and the data transfer rate in the direct channel, providing the desired degree of security of the wireless communication session.