Public spaces are central places in a community where people will gather to socialize and discuss politics or other community matters. Formal regulations on public spaces, where bylaws can be seen as a way to control for desired behaviour, have been used extensively in many cities. These regulations have actively excluded certain individuals from urban settlements and they continue to do so to create a clean space that is safe. This thesis uses urban comparison to contrast the four different local authorities of Auckland and Wellington, New Zealand and Calgary and Red Deer, Alberta, Canada using the response of homeless individuals to inform how different factors impact chronically homeless individuals in highly valued spaces. Interviews with homeless individuals, public servants, and enforcement officers can provide knowledge surrounding the regulation of these prime spaces. All of the chosen local authorities contain varying degrees of bylaws that impact the homeless lifeworld. Wellington has the fewest bylaws with Calgary and Red Deer having the most. It was found that the enforcement of those bylaws was a larger factor in how chronically homeless individuals respond to the bylaws. Enforcement of bylaws in Red Deer are the most severe out of all local authorities. Homeless individuals utilize different responses to remain in a lucrative space to counter the exclusion they face from the bylaws. Red Deer was seen more unlikely to be nonconfrontational because it was more likely to use persistence and voice. Through the most similar systems design, the factors that contribute to how homeless individuals respond to the regulation of prime spaces are discussed. It was found that a nonconfrontational response is more unlikely when there were more bylaws, enforcement was stricter, and the downtown core was not stable. Red Deer has been growing their downtown core to provide incentive for the global market to enter that local authority. This conscious growth increases the value the space holds. The research shows that the factors of downtown stability, the number of bylaws, and the enforcement of bylaws, all contributes to how homeless individuals respond to being excluded from prime spaces.