One of the most critical, yet inadequately explored, issues in lawyer client communication is the problem of explaining confidentiality, especially exceptions which permit or require the lawyer to disclose confidential information. Failure to disclose these exceptions results in misrepresentation to the client (e.g. "everything you tell me is confidential"), yet an accurate and complete explanation of the exceptions may inhibit the very trust that the right of confidentiality is intended to create. This article reports on the use of simulated interviews in the classroom to model an empirical approach to analyzing this problem that can be applied to law school clinics.