A brief critique of the evolution of ecological perspectives surrounding the current environmental crises in the age of climate age and Anthropogenic impacts is highlighted across the inter-disciplinary fields of landscape, urbanism, and ecology. First, revealing a paradox in the relationship between humans and nature through observations of “territorial rationalities,” concluding how we have transformed our planet into a state of “second nature.” Next, we propose a signifi- cant paradigm shift in how planning and design can be conceived based on McHarg’s approach in “design with nature,” and beyond it, towards a “territory subject” urging the necessity to address the social-ecological processes intrinsic in any territorial transformation through the lens of Political Ecology and Bio-politics. Lastly, our built environment’s currently complex and intertwined state is further explored and challenged through various project paradigms characteristic of the contemporary infrastructural complexity through the concept of “technonature.” Thus, three main hypotheses outline the body of this chapter to build on a stratified critical discourse: (1) Territorial rationalities, (2) Territory subject, and (3) Technonature. Across all sections, Discourses and projects develop the three hypotheses and rely on a vast set of urban and territorial research-by-design project-based methods intended not only as a testing ground for theories set elsewhere but as the very place where theory gets formed.