This chapter provides some aspects to probabilistic modelling in solving analytical problems of system engineering. The historically developed system of the formation of scientific bases of engineering calculations of characteristics of strength, stability, durability, reliability, survivability and safety is considered. The features of deterministic and probabilistic problems of evaluation of the characteristics of strength, stiffness, steadiness, durability and survivability are considered. Probabilistic problems of reliability, security, safety and risk assessment of engineering systems are formulated. Theoretical bases and methods of probabilistic modelling of engineering systems are stated. The main directions of solving the problems of ensuring security and safety according to the accident risk criteria are determined. The possibilities of probabilistic modelling methods in solving the problems of strength, reliability and safety of engineering systems are shown in practical examples.