This article explores the enabling factors and actors involved in the transformation pathways towards climate resilience of two German cities: Halle (Saale) and Mannheim. A specifically developed analytical framework served as basis for making the complex developments of the transformation paths of the two cities visible and comparable. The analysis has shown that despite strong similarities in terms of climate change impacts, the cities acted under very different political and economic conditions and thus applied particular strategic and tactical approaches and steering instruments. It can be stated that preparation of climate strategies, creation of a supporting central unit for climate issues and exemplary implementation of selected measures by the administration, as well as awareness-raising and cooperation with the stakeholders and citizens have played a key role in the cities’ transformation. In both cities, the city administration took the role of innovation organiser and orchestrated the pathway towards becoming climate resilient.