A professional practice instructor (PPI), as an evaluator of student performance in professional practice, makes important decisions as to whether nursing students are meeting course requirements. Several nursing education studies have reported that students whose performances are deemed unsatisfactory in professional practice courses nonetheless continue to receive passing grades. While this phenomenon, known as “failure to fail,” has been documented in studies involving nursing preceptors, it has yet to be the subject of an in-depth exploration among PPIs. Utilizing Gadamer’s (2011) philosophical hermeneutics and Fleming, Gaidys, and Robb’s (2003) hermeneutic methodology, this qualitative study sought to gain an in-depth understanding of the experiences of PPIs (n = 8) in evaluating unsatisfactory student performance within three educational institutions using a collaborative undergraduate nursing program (UNP) in Southern Ontario. This study revealed that evaluating unsatisfactory student performance is an emotionally draining experience for PPIs. The perception of an overwhelming workload and complex challenges can make it difficult for PPIs to assign a failing grade to a student, especially among novice PPIs. Furthermore, both assigning a failing grade and failing to fail students were found to have a negative impact on all participants in this study. Amid these difficulties, ongoing critical reflection and seeking collegial support and feedback were deemed helpful in validating a PPI’s decision-making, as well as alleviating the emotional aspects of grading experiences. While this study reinforces that stressors are inevitable when evaluating unsatisfactory student performance, they may be ameliorated through the creation of mandatory multi-modal orientation programs for all PPIs within educational nursing institutions. Furthermore, mentorship programs for novice PPIs might better prepare and support them in coping with the complex issues related to managing failing students. / Dissertation / Doctor of Philosophy (PhD)