Current-day psychiatric treatment of severely disturbed populations tends to focus on the biological, behavioral, and social dimensions of rehabilitation. This paper addresses the relative neglect of the complex psychodynamic and interpersonal aspects of treatment of individuals who are homeless and mentally ill by presenting two clinical cases that are discussed from various psychoanalytic frames of reference. Based on their clinical experiences, the authors conclude that psychoanalysis offers valuable frameworks to guide the treatment process and the structure of the treatment setting for individuals who are homeless and suffering from severe psychiatric illness.