This paper focuses on the performance of water distribution systems (WDSs) during long-term city transitions. A transition describes the pathway from an initial to a final planning stage including the structural and functional changes on the infrastructure over time. A methodology is presented where consecutive WDSs under changing conditions are automatically created, simulated and then analyzed at specific points in time during a transition process of several decades. Consequential WDS analyses include (a) uncertain network structure, (b) temporal and spatial demand variation and (c) network displacement. With the proposed approach, it is possible to identify robust WDS structures and critical points in time for which sufficient hydraulic and water quality requirements cannot be ensured to the customers. The approach is applied to a case study, where a WDS transition of epic dimensions is currently taking place due to a city relocation. The resulting necessity of its WDS transition is modelled with automatically created planning options for consecutive years of the transition process. For the investigated case study, we tested a traditional “doing-all-at-the-end” approach, where necessary pipe upgrades are performed at the last stages of the transition process. Results show that the sole design of the desired final-stage WDS is insufficient. Owing to the drastic network deconstruction and the stepwise “loss of capacity”, critical pipes must be redesigned at earlier stages to maintain acceptable service levels for most of the investigated future scenarios.