This chapter presents a reflective and critical deconstruction of my practice within the family shelter system in New York City. Specifically, it presents an analysis of tensions and contradictions in the enactment and impact of policies on individuals receiving services and the staff that serve them in the homelessness services and shelter systems. Shelter systems are fraught with practices that do not serve as part of the solution and perhaps are even part of the problem. These systems impose conditions and general mandates on clients and staff that can contradict social work values and ethics. There are many instances where the consequences of policies, mandates, and regulations serve to restrict the self-determination of clients, prevent the holistic improvement of their individual circumstances, and deviate from the humanistic values that can make a meaningful difference in addressing the needs of those who are homeless. Furthermore, the current system’s definition of success and its tools for tracking progress encourage staff to find short-term solutions to meet measurable goals, akin to approaches in the corporate sector. This chapter discusses the principles of anti-oppressive practice and shares examples of how practices and policies that are not aligned with an anti-oppressive frame can have devastating effects on individuals and ultimately serve to keep people in their disadvantaged state.