I argue that successfully addressing social problems such as homelessness requires that the vast and often hidden discretion afforded public officials be exposed, rehabilitated, and expanded. A more proactive bureaucratic role in implementing social welfare legislation ought to be tied to explicit normative underpinnings. State intervention to eliminate homelessness will only succeed if its goals are clear, if adequate resources are dedicated to the task, and if the public officials responsible for undertaking the intervention are empowered and directed to exercise their authority purposively as advocates on behalf of the homeless. This article is divided into four sections. In the first section, I briefly discuss the dimensions and dynamics of homelessness, emphasizing the changing nature of the public’s response to its most vulnerable citizens. In the second sections, I discuss how this evolving understanding of homelessness is reflected in the shifting priorities of public officials who interact with the homeless. In the third section, I maintain that discretion, as it is presently exercised and legitimated, relies on the disengagement of those affected in order for the administrative process to run smoothly. In the fourth section, I sketch an alternative framework of engagement, predicated on the belief that discretion is a social act. I conclude by briefly speculating on how a framework of engagement can be applied in the administration of shelters for the homeless. But first, I provide a brief overview of these components and how they are related.