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Agenda 21-inspired local visions and goals have not translated into actual local change. Increased interdependencies and interconnectedness at the global and other scales, inherent to varying degrees in all definitions of sustainable development, necessitate adopting a multi-level, multi-scale, multi-system, and integrated approach for analyzing the development and implementation of Agenda 21-based policies. Adopting such an approach this paper examines the causes for the failure by the Regional Municipality of Waterloo to meet its objectives on sustainability. The picture that emerges from this study is one of dissatisfaction with bureaucratic rhetoric, concerns about increased polarization, disagreement with the focus on economic growth at all costs, weak or inadequate regulatory tools to curb unsustainable activity, the size and complexity of problems to be addressed, unwillingness by politicians to take charge, inadequate discourse mechanisms, and there not having been a serious, acute local problem to rally everyone around a common goal and into action. This paper identifies “Systems-related Factors” and “Inter-relational Factors” as constituting barriers to sustainability at a regional scale. The paper concludes with a discussion of the implications of its findings for policy.