The hybrid method under consideration for assessing the financial sustainability of automated systems and enterprises in construction and engineering is based on an analysis of performance. It calculates the characteristics of instability in the course of operation, including estimates of the risk of bankruptcy of an enterprise. In assessing financial risks, multiple sources of information are taken into account: expert data on the interaction of factors in the production activity of enterprises and statistical data. A measure of risk assessment associated with the expected probability of deviation from the required level is introduced. Instability rates are calculated for each of the factors analyzed. On this basis, an integral measure of the risk of bankruptcy of the company is determined. This takes into account the interactions of factors, the scheme of which is set by the expert, and the values of impact assessments are clarified on the basis of expert data. The results of the calculations are presented in the point’s scale of the relationship. The sensitivity of the integral risk indicator to variations of instability of each factor or to variations of the factors themselves is also calculated. Sensitivity assessments allow us to form a management strategy aimed at improving the stability of the enterprise and minimizing the risk of bankruptcy of enterprises. Risk analysis procedures are designed to automate the state analysis processes of one or a group of enterprises and are focused on the implementation in information systems of different scales.