Confidentiality in counseling relationships helps ensure trust between clients and counselors. Yet, defining and understanding the boundaries of confidentiality in school settings is often difficult, as school counselors are engaged in multiple relationships with various stakeholders. This qualitative phenomenological study explores the experiences of nine practicing school counselors to answer the following two research questions: 1) how do professional school counselors respond to ethical issues related to student confidentiality as they perform their responsibilities within the school community? And, 2) how do school counselors believe members of the school community perceive student confidentiality? Upon analysis, two main themes emerged from participants' narratives: relationships and training. Subthemes were also present for each of the two main themes. Under relationships, subthemes include trust, school culture, teamwork and consultation. Under training, subthemes of graduate training, professional development, and experience emerged. Implications for counselor educators and school counseling graduate programs are discussed.