This volume reimagines the built environment not as a passive backdrop, but as a contested site where architecture, engineering, climate extremes, energy imperatives, and socio-economic inequalities converge. Sustainability is shown not as a universal mandate, but as a condition continually negotiated across uneven terrains of policy, design, and everyday inhabitation. Through contributions from leading scholars, the book examines Mediterranean cities to reveal the fractured foundations of the energy transition: fragmented regulations, misaligned certification systems, undervaluation of thermal performance, and urban fabrics that both resist and demand reinvention. Rejecting linear narratives and technocratic reductionism, the volume emphasizes the tensions between techno-optimism and the economic, infrastructural, and cultural inertias that delay transformation. Rather than offering prescriptive closure, it invites readers to grapple with contradictions that render the Mediterranean city both a site of impasse and a laboratory of renewal in the shadow of climate crisis.