Resilience is about dealing with the unexpected and the unprecedented. The very concept presumes some sort of disturbance or shock that distinguishes its field of operation from the more traditional concept of robustness. The prime issue of resilience research and parlance is not “why does it fail” but rather “why does it work.” Resilience is predominantly associated with the more generic matter of complexity. Hence, it is tempting to address the risk impact from resilience as a generic matter of complexity, ambiguity, and uncertainty about the future. The discussion may be deflected into a choice between a sheer probabilistic effect and an issue of uncertainty and lack of knowledge about the future. In this chapter, we understand the matter of resilience impact on risk as a matter of understanding the specific changes in operating conditions. An episode of successful adaptation is not a guarantee for the future. An “adaptive failure” may provide the ground for increased resilience by virtue of learning. Various strategies are explored, with special emphasis on a proxy approach as a means to sensitize risk assessments to implications of complexity and traces of presumed resilience.