In health care, efforts have been aimed at reducing medication errors rates; yet, medication errors continue to affect approximately 5% of hospitalized patients. In health care education, simulation provides nursing students a safe opportunity for hands-on medication administration, often including dosage calculation. However, the safety checks associated with medication administration—including the Five Rights—are frequently overlooked. Although the efforts aimed toward increasing medication safety include external factors (such as environmental measures and electronic resources), recent observations in simulation suggest a different problem. When medication orders are incorrect, many students do not know whom, how, or what to question to correct the mistake. This article describes two semesters with senior undergraduate nursing students in simulation and provides explanations, in their own words, for why they did not correct the mistake but caused a medication error instead. By recognizing and overcoming the barriers that inhibit questioning, educators can teach students how to form questions, whom to question, and when to ask questions.