Sustainable development is one of the key issues facing human survival on this planet. The urban planning discipline is actively involved in fostering more feasible ways to structure human activities and their relationship with the global ecosystem's finite resources. Since sustainability has become a major issue for human kind, sustainability assessments have proliferated in different ways to integrate socio-economic prosperity and provide environmental safeguards. In theory, these assessments can contribute towards addressing the increasing threats posed by climate change and by the depletion of natural resources, by building consensus around shared strategies involving a wide range of stakeholders to address national and international sustainable development goals. In practice however, sustainability assessments are undermined by problems associated with first the policy-making processes (for example, stakeholders' involvement) and second the measurement of the impacts of policies, plans and programs (such as the definition and computation of sustainability indicators). These issues weaken community trust in sustainability assessments and reduce their efficacy. Critical research is required to explore viable solutions.The main goal of this thesis is to address the shortcomings of current procedures for sustainability assessment. A comparative case study explores differences and similarities between an Australian region (South East Queensland) and an Italian region (Lombardia), which are representative of different institutional and planning backgrounds. Methodologically, this thesis develops and applies a framework to understand how limitations within political and societal processes prevent the achievement of environmentally sustainable planning. This framework combines a 'limits-oriented approach to evolutionary ecology' (Sih & Gleeson 1995) transposed to governance and policy-making processes, and the need to pursue a sustainable use of finite natural resources as suggested by positions addressing the 'limits to growth' by Meadows et al. (1972).Overall, this thesis develops an approach to diagnose current obstacles that need to be overcome and the pathway for achieving institutionalised limits-oriented approaches for improving procedures of sustainability assessment. This 'limits-oriented' framework outlines the benefits that South East Queensland and Lombardia can achieve by optimising current practices for sustainable planning within their regional contexts. This approach explores the limiting traits that undermine the performance of sustainability assessments, and proposes ways to bridge the gaps that separate their theoretical conceptualisation from their practical implementation.The framework developed and tested through this thesis offers an analytical lens to examine how the assessment of sustainable planning is currently featured in different institutional contexts. Its experimental implementation in countries with different planning traditions provides an insight on iii how to overcome iss...