A gap exists between recommendations to disclose errors to patients and current practice. This gap may reflect important, yet unanswered questions about implementing disclosure principles. We explore some of these unanswered questions by presenting three real cases that pose challenging disclosure dilemmas. The first case involves a pancreas transplant that failed due to the pancreas graft being discarded, an error that was not disclosed partly because the family did not ask clarifying questions. Relying on patient or family questions to determine the content of disclosure is problematic. We propose a standard of materiality that can help clinicians to decide what information to disclose. The second case involves a fatal diagnostic error that the patient's widower was unaware had happened. The error was not disclosed out of concern that disclosure would cause the widower more harm than good. This case highlights how institutions can overlook patients' and families' needs following errors and emphasizes that benevolent deception has little role in disclosure. Institutions should consider whether involving neutral third parties could make disclosures more patient centered. The third case presents an intraoperative cardiac arrest due to a large air embolism where uncertainty around the clinical event was high and complicated the disclosure. Uncertainty is common to many medical errors but should not deter open conversations with patients and families about what is and is not known about the event. Continued discussion within the medical profession about applying disclosure principles to real-world cases can help to better meet patients' and families' needs following medical errors.