In this paper, the authors propose two complementary approaches in an attempt to contribute to systems-of-systems (SoS) safety evaluation through resilience assessment. The first approach is a risk monitoring design, it is conceived to monitor, evaluate and analyze risks that represent destabilizations’ catalyzers. The second one is a structural analysis that begins with the estimation of criticality and frailty levels which leads to the calculation of failure impact and susceptibility measures of a component system on/to the SoS performance and process continuity. The combination of these approaches helps to assess SoS resilience through building a futurist, quantitative and anticipative perspective to evaluate the potential risks, their influences and impacts on SoS structure. Accordingly, this embraces a step towards safety forecast, evaluation and enhancement. A case study of a real-based economic infrastructure of a geographic area in France approached as a SoS model, is provided to experiment the proposition. The outcome of the presented approach’s application shows that: (1) the use of the risk’s monitoring dashboard helps to qualitatively illustrate risks striking the SoS or could possibly affect it in the future; (2) the structural analysis evaluates the impact of a component system’s failure on the overall performance and efficiency of the SoS embracing it and vice versa; (3) the proposed approach could be used for anticipative and preventive reasons.