This article presents a Canadian perspective on the issue of failure to fail in Bachelor of Education programs. The issue of failure to fail in Bachelor of Education programs is one that had not been explored in any great detail. What literature does exist focuses on the strain that a teacher experiences when s/he mentors a student teacher (Siebert, Clark, Kilbridge, & Peterson, 2006) and the wide variety of situations that can result in failure (Sudzina & Knowles, 1992). This study examines whether the issue of failure to fail in final pre-service practica exist and, if so, why? Twelve interviews were conducted at a mid-sized Canadian university in Ontario with university supervisors and associate teachers on the topic of teacher candidate failure during the final teaching practicum. All participants had experience with teacher candidates struggling during practicum. Faculty commented on their supervision of student teachers in Ontario, other provinces in Canada, and the United States. Results indicate that both university supervisors and associate teachers find the decision to fail a student teacher difficult, taking an emotional toll on both the supervisor and the student. University faculty report the decision to fail results in additional work for the faculty responsible; however, failure to fail an underperforming student teacher could diminish the reputation of professional programs. Associate teachers feel a sense of betrayal when their recommendations to fail an under-performing student are not followed by the university. These findings have implications for improving the quality of field experiences and support for students, associate teachers, and faculty in Bachelor of Education programs.