This research aims to examine the perceptual gap between urban managers and homeless individuals in their encounter with the phenomenon of homelessness in Tehran. The study was conducted using a qualitative approach and narrative inquiry methodology. Data were collected through in-depth interviews with urban managers and homeless individuals, field observations, and documentary sources, and analyzed employing thematic analysis. The findings reveal the existence of a fundamental gap in the understanding and conceptualization of the issue; such that urban managers predominantly perceive homelessness as a security concern linked to urban order, emphasizing control, management, and cleansing strategies for the urban environment. In contrast, homeless individuals regard this condition as a consequence of structural exclusion, systematic poverty, and the violation of their citizenship rights. They demand recognition of their human dignity and civic status, beyond merely receiving supportive services. This perceptual divergence explains the ineffectiveness of purely security-oriented policies and the perpetuation of the homelessness cycle. Accordingly, the research concludes that exiting the current situation necessitates a paradigmatic shift from coercive and regulatory approaches to human-centered, empowering policies grounded in social justice—an approach that begins by listening to the voices of the marginalized and redefining the issue based on their lived experiences.