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Cities face unprecedented challenges and opportunities. The challenges include the need to tackle phenomena from climate change to population growth, as well as how to bring the European Union (EU) closer to the goal of climate neutrality by reducing carbon emissions. The political-institutional focus to resolve these issues is urgently required. The interventions that are needed in cities to meet the Green Deal objectives are numerous and diverse (including energy, transport, nature and biodiversity, food and agriculture, green finance, as well as with respect to the circular economy [CE]). Diverse approaches are justified, to an extent, as the starting point is not the same for all cities involved in the transition (large, medium and small) and reaction capacities are different. Diversity can cause confusion, however, and this has been found in particular with so-called circular cities; the absence of a defined intervention model has caused some cities to adopt both narrow and wider visions, leading to many 'circular imaginary' cities. The origins of these visions have stemmed from the industrial rather than the urban context, with several adaptations being made. This paper starts by discussing the journey to sustainable cities — in particular the role of circular cities in the Green Deal — and then explores the existence or lack of strategies for circular cities. Amsterdam and Milan are used as case studies to explore whether and when circular cities can be considered cornerstones of the ecological transition. [ABSTRACT FROM AUTHOR]