This thesis builds off of interviews with former members of Chicago’s Uptown Tent City to add to our understanding of the homeless community’s relationship with the shelter system. It finds that many individuals were either barred or alienated from shelters due to often-necessary rules and restrictions stemming from concerns about residents’ safety and shelters’ limited resources. Tent City grew as a response to shelters’ inadequacy by a community in search of more autonomy and agency. The community was quickly forced to adopt many similarly restrictive rules to protect residents and ensure the encampment’s continued existence; however it also provided its members with potent political agency to advocate for their needs. Some recommendations are made on making shelters more accessible, but the necessary nature of many of the shelters’ exclusionary regulations reveals the need for cities to recognize homeless encampments as inevitable and to harness their political potential by collaborating with residents to respond to their needs.