The purpose of the study was to review court cases about privilege and confidentiality for caring professionals and their clients, in an effort to understand the extent of privilege for school counselors and confidentiality for their students. The research questions guiding the study focused on the issues, outcomes, and trends in court cases about privilege and confidentiality for caring professionals and their clients in the timeframe of 1956-2014 to inform the development of privilege and confidentiality for school counselors and school children. The courts cases were obtained from Westlaw™ Reporter System, 1956-2014, under the category of caring professionals. This was a document-based, qualitative study, approached from a historical perspective. The documents that were studied in this qualitative research are court cases. The court cases followed the Statksy and Wernet’s (1995) format to help analysis for issues, outcomes, and trends in the opinions rendered by the courts. Results of the study, suggest that many of the cases represent the courts attempt to balance the demands of the Fifth Amendment, Sixth Amendment, State Statutes, and the United States Supreme Court Jaffee v. Redmond (1996) legal precedent. The issues, decisional outcomes, and trends for caring professionals’ court cases established that courts recognize the important of privileged communication and confidentiality among caring professionals, as well as the fact the courts did not overstep the privilege entrusted to those caring professionals and to mental health records, and narrow guidelines directed state’s privilege statutes. State’s privilege statutes shared little standardization across states. Licensed psychotherapists and school psychologists share the same level of privilege as the law provides for the attorney-client iii privilege. The results from the study emphasized society’s value of mental health record privacy and psychologist-patient privilege. Other caring professionals have reached society’s value of privilege in communication as social workers and school psychologists. Licensures have elevated the counseling profession. Even though other caring professionals run parallel to school counselors in issues with students, school counselors have not been accorded privilege. The future holds a place for school counselors to evaluate the certification of counseling in education to autonomy through licensure, then reaching privilege in communication and confidentiality.