To explore the experiences of general practitioners who continue to sit a highly-competitive residency entrance examination, despite repeated failure. This qualitative, exploratory study employed semi-structured, in-depth interviews with ۳۵ candidates of a residency entrance exam who had failed the examination at least twice and were preparing to sit it again. Interview questions addressed the challenges they faced and how they managed these challenges. Interview data were audiotaped, transcribed, and analysed to identify themes. The results demonstrated that more than ۵۰% (n=۱۹) of candidates struggled continuously and internally with different aspects of the exam. These include being under a great deal of pressure to succeed, failing to prioritize study materials, inefficient review during the final days of preparation, and sitting the exam with an afflicted body. Furthermore, during the examination, they frequently used inefficient strategies to answer questions. Afterwards, they experienced feelings of freedom associated with having finished the exam. Participation in a highly-competitive examination exerts a considerable amount pressure on low-performing candidates. This climate not only results in burn out of participants, but it also influences their learning styles and identities as future physicians. It is therefore necessary to design a syllabus for both test candidates and policy makers, in order better to manage this environment. Candidates also should be aware of their individual weaknesses, in order to improve their studying skills.