The objectives of the presented paper are to better understand the mechanism of failure development in the dynamic mechanical systems. It is important to consider carefully the present changes in a technical conditions of elements of the system when planning the requirements to a proactive risk managements strategy. While a dynamical system traditionally is modeled by structural decomposition, in the paper the dynamic behavior of system is modeled by decomposition of the behavior flow into events and errors accompanying occurrence of failure. From this point of view the nonlinear model of failure occurrence, made from Volterra Series, is analyzed to realizing long term benefits of a proactive maintenance strategy. The models describes the effect on the evolution at the process variables for each hypothesized fault failure. In the paper it is also analyzed the impact of nonlinearity of the sub-section on the behavior of the whole system by using of high-order spectra.