Despite practice supervision in paramedicine contributing to 50% of undergraduate programmes, there is currently no national mentorship framework in place. With the issue of failure to fail reported within other disciplines, there is limited research around this phenomenon in the field of paramedicine. To explore the factors that contribute to failure to fail undergraduate students in the practice setting to identify the implications for paramedic mentorship. A systematic review of the literature was conducted to identify primary qualitative research. Articles with a range of study designs were identified and included within the review. A total of 2,368 records were retrieved following the search. Seventy-six full article screens were conducted which resulted in 11 high-quality articles for inclusion within the study. The systematic review identified a variety of multifactorial challenges faced by mentors. These can be broadly categorised into three main themes: emotional impact, external pressures, and inconsistency. Many of the challenges related to the mentors' lack of self-confidence in making accurate assessments of competence. Given the multifactorial challenges faced by mentors, failing to fail, ongoing training and support from HEI's may reduce some of the challenges and standardise mentorship within the profession. Nationally, implementing a framework for mentorship in paramedicine should be considered.