<p>In designing and managing various types of complex systems, the identification, modeling, evaluation, optimization, and management of potential risks are of great importance. Numerous risk assessment methods are available, and their selection depends on the specifics of the enterprise, organization, or project. Often, a combination of different methods is employed to achieve a comprehensive risk evaluation. Existing risk assessment models primarily focus on representing risk probability and impact, which are typically evaluated using scoring or other techniques. In this paper, a different approach to risk assessment is proposed, which is based on logical-probabilistic methods. In order to assess the risks and safety indicators of complex systems, we use the method of describing the scenario of the system transitioning into a hazardous state with a logical function, the logical elements of which are risk-initiating events and conditions. Using logical-probabilistic methods, the logical function of a scenario can be transformed into a probabilistic representation, which allows for probabilistic assessments of risks and safety. This helps us to identify the weak points of the system, to quantify the threat and security, to perceive the risks as a whole, to optimize the risks, to plan preventive actions, etc. As an example, the article discusses the issues of the logical-probabilistic modeling of scenarios for implementation risks of enterprise resource planning systems, the methods of transforming a logical function into a probabilistic expression, and the examples of quantitative risk assessment under the conditions of using Agile and Waterfall project management methodologies.</p>