Based on the critical analysis of the evolution of spatial and urban planning in Serbia through four phases of evolutionary resilience (growth, conservation, destruction, and reorganisation), this chapter compares planning approaches during socialist Yugoslavia and post-socialist Serbia. The comparison focuses on three key factors: systemic (institutional and regulatory frameworks), networking (horizontal cooperation among stakeholders), and professional (interdisciplinary integration). The findings challenge conventional assumptions about democratic transition and planning progress, revealing that the shift to democracy in Serbia and embracing the neoliberal paradigm did not automatically enhance planning resilience. Paradoxically, the socialist system demonstrated more resilient characteristics in certain aspects, particularly in public participation and interdisciplinary cooperation. Nevertheless, this comparative analysis indicates that comprehensive planning resilience requires more than isolated participatory elements or technical competence; it demands an integrated framework where political structures enable rather than constrain adaptive capacity. By examining how neither system fully achieved planning resilience—socialist planning limited by ideological boundaries, democratic planning undermined by neoliberal pressures—these insights contribute to critical discourses on post-socialist transition, challenging simplified narratives about the relationship between political systems and planning effectiveness.