For people who are disenfranchised from society for other reasons, especially homelessness, a paranoid delusional system can create an additional obstacle in the therapeutic engagement and treatment of such individuals. In this article, we describe a composite case of a homeless woman with paranoid schizophrenia. Through this case example, we will explore various obstacles to treatment and discuss strategies to overcome these hurdles to treatment, initiate a therapeutic alliance, and further facilitate and maintain therapy.