This paper investigates problems related to supply chain risk identification and simulation-based risk assessment. Accordingly, the paper is divided into two logical parts. The first part represents earlier researches about risk recognition within the sphere of supply chains. The distinction between terms “uncertainty” and “risk” is discussed. Based on the predefined supply chain functions, risk is recognized as possible disruptions that can affect supply chain’s ability to function normally. Thus, it is advised to use a system reliability analysis as an approach to supply chain risk assessment. Within the second part of the paper, the use of simulation is advised as an effective approach for supply chains reliability evaluation. A simplified supply chain system is defined and corresponding supply chain reliability simulation model is created. Simulation results are validated using a mathematical description that proves the adequacy and effectiveness of simulation application. Then, it is stated that the mathematical reliability models application is limited due to potential complicity and risk quantification features.