An experimental urban research work based on Frei Otto and Eda Schaur's thoughts on unplanned settlements, and on the form-finding experiences carried out at IL, suggests that today the act of design can benefit from a deeper understanding of the natural processes of occupation and connection. Presently there is a progressive tendency to incorporate parametric design strategies in urban planning and design. Although the computational technologies that allow it are recent, fundamental theories and thinking processes behind it can be traced back to the work conducted at the Institute for Lightweight Structures (IL) in Stuttgart, between the 1960’s and 1980’s. This paper describes an experimental urban research work based on Frei Otto and Eda Schaur's thoughts on unplanned settlements, and on the form-finding experiences carried out at IL. By exploring the digital development of parametric and algorithmic interactive models, two urban design proposals were developed for a site in Porto city. Out of this experience, this paper suggests that today the act of design can benefit from a deeper understanding of the natural processes of occupation and connection.