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ABSTRACT Using in-depth face-to-face interviews, this study explored 34 homeless shelter workers’ perceptions of homelessness and working with the homeless. We asked the following questions: 1) What were the barriers that homeless shelter residents faced in combating homelessness, from the perspective of the homeless shelter workers? 2) What were the challenges that homeless shelter workers encountered in working with this at-risk population? Our findings shared the realities that the homeless population faced from the lens of shelter workers with different job responsibilities (ranging from customer service workers to case managers, program directors/coordinators, and shelter administrators). Overall, we found that working with the homeless community could present a challenge for shelter workers given the limited availability of funding, discrepancies in agreement of solutions, the lack of qualified helping professionals, the limits of service coordination, preconceived judgment/prejudice from the public, and a series of obstacles that the homeless population faces including barriers to accessing services, employability, personal hardship, and social stigma.