Urban sustainability and sustainable development have permeated both public and academic discourse since the 1980s Brundtland Commission Report. The report defined sustainability and situated it within social, economic, and environmental factors emphasizing sustainable development as a path forward. Academics, scientists, and policy makers undertook the task over the subsequent decades to define sustainability, operationalize it, measure it, and monitor it. However, despite the rapid progress and leaps in understanding the discourse has its weaknesses, its singular focus on particular elements of sustainability systems, its lack of cross level examination across scalar divides, its primarily urban focus, and its majority functionalist approach. These weaknesses leave a void in the understanding of urban sustainability as an element of an economic, social, and environmental interconnected urban-rural system. A subfield is emerging to understand this interconnectedness of sustainability through examining the built environment and the urban-rural divide. However, currently, Canada is largely absent from this subfield’s exploration. In order to expand this exploration and analyze the sustainability interconnections within Canada through the urban built environment, the Leadership in Energy and Environmental Design (LEED) certification will be a key element going forward, because LEED is a globally accepted green building certification system that is primarily utilized in North America. This research thesis contributes, as a substantive text, to this subfield through answering the main question left open by current discourses: Are there any discrepancies between the projected sustainability of LEED projects and the actual sustainability realities of the projects? With further queries being posited: What is the sustainability reality of the LEED buildings; what are the sustainability realities of the users/tenants within the LEED buildings; and, what is the sustainability reality of the LEED buildings across the urban-rural divide? I garnered the answers through a mixed quantitative/qualitative analysis of case studies within the Canadian urban built environment: LEED projects. The projects will be examined utilizing an urban metabolic analysis of the quantitative data and a point-based scoring system adapted from a Strengths, Weaknesses, Opportunities, and Threats analysis (SWOT) I named Focus Factor Analysis to quantify qualitative elements of the projects. Consequently, the analysis will also highlight connections between the urban area projects and the rural surroundings using a combination of databases and LEED, corporate, and government reports. Discrepancies have been found and although the LEED projects are sustainable on the local level on a network level they are not.