To increase the security of modern, volatile supply chains a proactive risk management based on real-time risk related information transparency is required. At this time, none or only limited empirical/objective information about digitalization benefits for supply chain risk management is available. A method is needed, which draws conclusion on the estimation of costs and benefits of digitalization initiatives. The paper presents a flexible simulationbased approach for evaluating digitalization scenarios prior to realization. The evaluation approach is integrated into a framework and its applicability will be shown in a case study of a German steel producer, evaluating digitalization effects on the Mean Lead time-at-risk.