The city, a place of contemporary living par excellence, challenges the planner by making it necessary to adapt progressively quicker to changes and to overcome the traditional design approach linked to the modern idea of the industrial city. Indeed, living in non-stationary contexts, the complexity of problems nowadays requires a new planning endeavor capable of testing future solutions ‘in the field’ rather than ‘on paper,’ involving citizens, but also continuously adapting processes to achieve the expected results. The proposed contribution aims to document possible ways to trigger virtuous urban renewal processes, sustainably activating tangible and intangible resources. The topic will be investigated from the point of view of the triad: ‘project, technology, and digital solutions,’ adopting a social perspective. The latter ensures the active involvement of citizens in strategic decisions, increasing their awareness and civic sense, but also supporting the proposition of evolving planning scenarios in order to develop solutions that will be concrete, achievable, and resilient. The core element concerns the way in which it is possible to promote the creation of an extended social mind through which collective behavioral change can be fostered. In some cases, digital technologies prove to be the effective ‘expert instrument,’ also for understanding the planned intervention, opening the design process for different stakeholders not necessarily familiar with technical conventions. According to Floridi, digital transformation ‘disconnects and reconnects specific processes,’ and the project represents the most powerful innovation element to promote the ecological transition. These dynamics will be explored through the analysis of some research and project activities that directly involved the authors of this article.