Rapid urbanization and the intensification of climate hazards highlight the necessity of rethinking urban energy efficiency beyond the single-building scale, with a distinct emphasis on biophilic strategies. However, the complex mechanisms linking these interventions to energy performance, along with their underlying contextual barriers, remain underexplored. The present study aims to elucidate the contextual and multi-scalar mechanisms linking biophilic architecture and urbanism with urban energy efficiency in Tehran’s District 22. Conducted within an interpretivist paradigm using an inductive qualitative approach, data was gathered through 17 in-depth expert interviews. Participants were selected via purposive and snowball sampling until theoretical saturation was achieved. Systematic data analysis was performed utilizing the six-phase thematic analysis method, supported by qualitative data analysis (QDA) software. The findings revealed that the energy-oriented effectiveness of biophilia necessitates a transition from decorative elements to active metabolic infrastructures, operating through physical modifications of the urban boundary layer, the reduction of radiant temperature, and the facilitation of adaptive comfort. Furthermore, it was identified that the cascading transfer of these effects within the morphological context of District 22, when confronting deep-rooted institutional barriers—such as full-plot excavation regulations for parking, the subordination of nature to real estate logic, and water resource constraints—has led to phenomena such as wind shadows and ecological traps. The results indicate that realizing urban energy efficiency requires a paradigm shift in urban management from prescriptive regulations to performance-based governance. Mandating pre-construction climatic assessments and adopting decentralized water management policies are essential to avoid maladaptation while guaranteeing spatial justice and citizens' climate rights.