This chapter explores the multiple meanings of homelessness and the clinical social worker's interventions based on a postmodern relational framework. It begins by discussing macro etiologies and their deleterious effects of being homeless. The chapter then provides specific and nonspecific interventions with people who experience homelessness. A case example is utilized to highlight the challenges of the clinical social worker's ability to stay attuned to the multiple meanings of experiences in a life of homelessness and the management of countertransference in the face of extreme duress. It argues for the realignment of how the clinical social worker frames an understanding of homelessness, shaping the relational stance with a client suffering from this abhorrent social condition.