According to the American School Counseling Association’s school counseling competencies and the Council for Accreditation of Counseling and Related Educational Program’s standards, school counselors should have skills, abilities, and attitudes to address complex and authentic problems in their practice. Yet, school counselors often do not feel prepared by their preparation programs in being able to address the realities of their practice. Problem Based Learning activities, such as the one proposed in this article, may help school counselors-in-training develop the skills in internship supervision to address complex problems they will face in their future work. Implementation guidelines, a case example, and limitations of this activity are provided.