Systems are always embedded in environments with which they interact and which influence their behaviour—sometimes to a limited extent, but often in a formative way. This also applies to the resilience behaviour of energy systems, which means that the resilience of an energy system can never be solely a property of the system itself and its architecture, but also arises or fails as a product of the interaction between system and context. The chapter describes the analytical gaps that result from disregarding the system-context problem and some approaches to dealing with the system-context problem that can be observed in practice. The context-scenario approach is then presented in more detail and its application in the ReMoDigital project is outlined.