The primary goal of classroom assessment is the improvement of student learning rather than the evaluation of teaching through observation. Many formative assessment techniques, including the group instructional feedback technique (GIFT), electronic mail feedback, and small group instructional diagnosis, carry an implicit or explicit promise of confidentiality Although this confidentiality usually serves a vital purpose in the assessment process, situations may arise in which maintaining confidentiality could have detrimental effects or legal consequences. The Excellence in Learning and Teaching Initiative at Southern Illinois University Edwardsville has operated a successful GIFT program that has grown to include trained faculty assessors from various departments. GIFT is a technique that centers on obtaining student responses to questions related to their learning in the classroom. Like psychotherapists, classroom assessors may occasionally encounter information indicating that students are being treated in a manner that makes them vulnerable to harm, danger, or exploitation. Moreover, when the assessor encounters such information, he or she may incur some legal obligations to act, and failure to act may expose him or her as well as his or her institution to liability. In such cases, breaking confidentiality may be preferable to maintaining it. Specifically, informing an appropriate administrator or supervisor of the teacher's behavior may prevent further harm to students. In this article, some examples from the authors' experiences on their university's GIFT team illustrate how the question of breaking or maintaining confidentiality may arise. (These examples are fictional but have a basis in actual GIFT experiences. They have been altered to protect the identities of the individuals involved.)