Abilities of "smart systems" for processing information, adaptation to conditions of uncertainty, and performance of scientifically proven preventive actions in real time are analyzed. Basic probabilistic models and technologies for the analysis of complex systems, using "smart systems," ways of generation of probabilistic models for prognostic researches of the new systems projected, modernized, or transformed, are proposed. The proposed methods are described to predict risks to lose integrity for complex structures on the given prognostic time and rationale of preventive measures considering admissible risk, estimate "smart system" operation quality, and predict in real time the mean residual time before the next parameter abnormalities. The methods and technologies are implemented on the level of the remote monitoring systems. The application is illustrated on the examples of the jointstock company "Siberian Coal Energy Company."