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The need for outreach psychotherapists has increased considerably over the past few decades. Research suggests graduate training has not kept up with this phenomenon. Graduate students continue to be trained for in-clinic work, and are not prepared for the challenges of going into clients' homes and into the community. The literature supports the necessity for therapists who will be doing outreach psychotherapy to be trained in working in these atypical settings, as many innate challenges exist in this work. Challenging mental health issues, distracting environmental issues, safety concerns, lack of collegial support and supervision in the field, feelings of isolation, role confusion, countertransference, and blurred boundaries are just some of these concerns. This article reviews the literature of a number of key topics critical to competent and confident work in the community. Confidentiality, boundaries in clinical practice, managing countertransference in the therapy experience, self-disclosure, dual-relationships, and safety are all explored through the lens of outreach psychotherapy. Training graduate students in these areas is critical to reducing burnout and boundary violations with this vulnerable client population.