Background <p>Imposter syndrome (IS) is a psychological pattern involving persistent self-doubt and fear of being exposed as a “fraud” despite objective achievements. Fear of failure (FOF) is a significant psychological factor.</p> Objective <p>To investigate the association between fear of failure and impostor syndrome among undergraduate medical students in Pakistan.</p> Methods <p>This cross-sectional study included 157 MBBS students from all five academic years at the Khyber Medical College in Peshawar. Impostor syndrome was assessed using the Clance Impostor Phenomenon Scale (CIPS), and fear of failure was evaluated using a single-item Likert question. Chi-square tests were used to determine the associations.</p> Results <p>The prevalence of IS was 51.0% (95% CI: 43.2%–58.8%). A significant association was found between FOF and IS severity (χ² = 24.579, <i>p</i> = 0.017). Students with higher FOF were more likely to report frequent or intense IS use. No significant associations were found between sex and the educational background of the participants. Second-year students had the highest prevalence of IS (61.5%).</p> Conclusion <p>Fear of failure is significantly associated with the presence of imposter syndrome among medical students. Early identification and targeted interventions may reduce distress and improve students’ academic well-being.</p>