The paper explores how the reflection on urban scale digitals twins and the debates about the role of commoning practices in architecture and urban planning could be combined in a way that would address climate justice and social justice simultaneously. At the core of the paper is the idea that sustainable environmental design and regenerative design necessarily involve an exploration of how one can re-conceive the redistribution of wealth, land, and power. The paper examines the role of digital twins in predicting the characteristics of ‘leisurescapes’ and ‘carescapes’. Particular emphasis is placed on the potential of the utilization of urban scale digital twins by policymakers while deciding the branding strategies concerning the creation of sites destined for recreation and care. The paper also explores the role of care and recreation in re-thinking city branding and the ways in which urban scale digital twins can contribute to such endeavors. One of the main objectives of the paper is to shed light on how urban scale digital twins can contribute to the combination of “city branding” and sustainable development. In parallel, it examines how “city branding” can serve in establishing urban regeneration strategies. Another issue that is investigated is the role of urban scale digital twins in the “calibration” or the balancing of the tension between the so-called “city branding” and the so-called “city commoning”. A tension that is useful for better grasping the notion of commons is the interrogation regarding the understanding of commons as community or as public space.