Recent years have seen fundamental shifts in the objectives and delivery of assistance to the homeless. An early emphasis on emergency shelter and monetary housing assistance has been replaced by a focus on programs designed to blend shelter with an array of social services. In most instances, however, programs combining shelter and social services are designed as transitional; that is, they are intended to help homeless individuals and families move from a position of dependence to one where they can live “independently.” The emphasis in transitional housing programs is on making homeless people “housing ready.” This paper concerns the process of assessing “housing readiness” as observed during eighteen months of fieldwork in a federally supported transitional housing program for formerly homeless single adults. The detailed case study that follows supports three important findings. First, there was virtual unanimity among staff and residents that substance abuse was the cause of their homelessness and the key to its solution. Second, success within the program was defined and operationalized along very specific but well understood normative dimensions that have little to do with the material circumstances in which residents find themselves and everything to do with “recovery.” Third, “recovery”—the key to housing readiness in this environment—was measured not by objective measures, i.e., number of months sober, but rather by what was widely referred to as one's “quality of sobriety,” a subjective and consequently often hotly debated measure of attitude and outlook only loosely related to demonstrable abstinence from alcohol. This last finding, that ultimately housing readiness is a subjective judgment, both increases the discretion of shelter staff and generates a systematic disattention to the individual economic issues that are fundamental to an exit from homelessness.