Over 35000 Canadians experience homelessness on any given night (Raising the Roof 2015). Often subtle design interventions in the urban environment serve to exclude these persons from having a place to rest. This thesis explores the use of exclusionary design in a mid-sized Canadian city, Guelph, Ontario. First, a visual survey of hostile elements in downtown Guelph depicting the frequency of exclusionary design was created. Next, seven semi-structured interviews with official actors involved in the design and regulation of public space are compared and contrasted to eight interviews with social service providers who provide services to homeless populations. This qualitative interview data allows for a deep exploration of the justifications, visibility, impacts, and (un)success of exclusionary design. Finally, employing a Right to the City framework throughout this study that centers the rights of those experiencing homelessness to inhabit public spaces, alternative suggestions to excluding vulnerable populations from public spaces are explored.