The recent works on the Velasca Tower have prompted a reflection on the methodological approach for the intervention on the Milanese "skyscrapers" which are demonstrating an intrinsic fragility with the passage of time and are no longer capable of responding to the needs of contemporary society. In the first part, the conference—part of Milano Arch Week 2024—addresses the theme of the relationship between the project and history, in particular for the Velasca Tower considering the studies dedicated to it over the various decades both at a national and international level and the importance of a rereading of the archive material. In the second part the debate will focus on contemporary interventions that have affected some tall Milanese buildings, such as the Torre della Permanente, the Garibaldi Towers or the Turati Tower, which are relevant from a historical point of view, fully vital places that have defined the face of the city.