Land is a complex, dynamic and adaptive system, where its socio-ecological interactions create continuous land processes that provide multifunctional values to society. Overlooking this dynamic condition and these multiple values – and their trade-offs – within decision making processes, as is the case in territorial planning, compromises these values and they are irreversibly lost, decreasing the resilience of our territories. The following body of work discusses the potentials of current digital tools by proposing a framework capable of understanding these complex interactions in a dynamic way. A computational pipeline and feedback-loop methodology is proposed and tested in the case study of Vitoria-Gasteiz municipality. The resulting Decision Support System enables a new spatial planning methodology capable of measuring land resilience for climate adaptive planning.