The transformation of the rating and certification system alternatives that have come to characterize the green building movement, inundate the real estate market, and promote sustainable development across the globe, is demonstrative of a collective scaling up. There is a clear indication that the paradigm of sustainability assessment tools is changing from the building scale to the built environment scale (Castanheira, 2013) This thesis examines the emergence and evolution of the alternative sustainability assessment and rating systems in their agenda to expand in scope and scale with increasing evaluation weight for connections beyond the building, beyond the site, and ultimately planning and urban design operatives. A recent trend in practice has been to approach community planning through the sustainability lens, and there has been a recent outpour of capability building in efforts to leverage sustainability assessment tools as planning assets. But there are still many barriers and bottlenecks attributing to a relatively slow movement from theory to practice. Bridging those gaps is a process that could potentially benefit greatly from increased collaboration with planners and vice versa.