The relationship between clinical supervisor and supervisee is fraught with ethical concerns, as the supervisor serves multiple functions within the relationship. The supervisor has a responsibility to evaluate and foster the supervisee’s professional and clinical growth and development. Additionally, the supervisor has a responsibility to serve as a gatekeeper to the profession and consider the welfare of the supervisee’s current and future clients. The case of Sasha and Hector presents numerous ethical issues to be processed dually with separate regard given to the supervisor-supervisee relationship and the counselor-client relationship. The University of New Orleans Doctoral Ethics Team analyzed and evaluated possible courses of action to aid in resolution of these presented dilemmas. In doing so, the team reviewed current scholarly literature and applied appropriate ethical codes in the context of an ethical decision-making model. The team concluded by offering recommendations within the context of pertinent legal, ethical, and moral codes.