Summary Background The ‘failure to fail’ phenomenon has been reported in studies involving preceptors and students in nursing and in other practice professions, but it has yet to be the subject of exploration among clinical nursing instructors. Research has revealed that assigning a failing grade in a practice profession is not always a straightforward task; however, passing students who are incompetent in their nursing practice could have a deleterious impact on the quality and delivery of patient care. Methods The author interviewed eight clinical instructors who had failed unsatisfactory students to gain an in‐depth understanding of each instructor's experience in evaluating these students. Gadamer's hermeneutic principles were used to interpret the interview texts and dialogue with the participants through the hermeneutic circle of understanding, use of the researcher's prior experience and openness to new understanding. Findings The experiences of the clinical instructors in this study suggest that they have struggled with their emotions, particularly when they were novices, during the multiple personal, professional and organisational challenges that they have encountered within their teaching roles and responsibilities. Discussion The difficulties and challenges highlighted in this study may offer insight for academic stakeholders in nursing schools on how to mitigate these issues through developing an onboarding orientation and mentorship programme that will support faculty member development in the evaluation of unsatisfactory student performance.