Student confidentiality can create challenges for both school counselors and administrators. The article addresses historical and ethical issues surrounding confidentiality in schools as well as methods of working toward collaboration. Developing an understanding of one another's ethical, legal, and professional responsibilities can lead to a collaborative and cohesive working alliance. The article tailors strategies at the per-service training, district, and individual levels to create an environment in which administrators and counselors can establish, enhance, or rejuvenate a collaborative relationship.