Background <p>Malpractice litigation is increasingly prevalent in contemporary healthcare and may influence both clinical decision-making and physicians’ psychological well-being. The present study aims to evaluate the fear of malpractice and career decision regret among resident physicians and to identify factors associated with these constructs.</p> Methods <p>A total of 308 resident physicians (87.7% of the eligible population) from surgical and non-surgical clinical specialties at a university hospital in Turkey were included. Fear of malpractice was assessed via the Malpractice Fear Scale, and career decision regret was assessed via the Decision Regret Scale. We collected data on sociodemographic characteristics, specialty preferences, and exposure to malpractice complaints. Multivariate linear regression identified independent predictors of fear of malpractice and career decision regret. </p> Results <p>High levels of fear of malpractice were reported by 73.1% of the residents, and 73.4% experienced varying degrees of career decision regret, predominantly mild regret (44.2%). Fear of malpractice and career decision regret were modestly (r_s = 0.228, <i>p</i> &lt; 0.001) but significantly associated. Higher fear of malpractice scores (<i>β</i> = 0.178, <i>p =</i> 0.001) and prior personal exposure to malpractice complaints (<i>β</i> = 0.132, <i>p</i> = 0.017) independently predict increased career decision regret. Awareness of colleagues accused of malpractice was strongly associated with greater fear of malpractice (<i>β</i> = 0.219, <i>p</i> &lt; 0.001). Intrinsic motivations, including interest in the chosen specialty (<i>β</i> = −0.176, <i>p</i> = 0.001) and professional satisfaction (<i>β</i> = −0.147, <i>p</i> = 0.007), were associated with lower career decision regret. No significant differences in fear of malpractice were observed between residents in surgical and non-surgical clinical specialties (<i>p</i> = 0.227).</p> Conclusions <p>Fear of malpractice is a prevalent stressor among resident physicians and is significantly associated with career decision regret. While malpractice-related experiences may increase regret, intrinsic motivations for specialty choice—particularly personal interest and professional satisfaction—appear to buffer against career decision regret. These findings suggest that strengthening both medicolegal support and factors that promote professional fulfillment may help improve residents’ career well-being. Integrating medicolegal education, psychological support, and institutional risk-management strategies into residency programs may help mitigate these adverse effects.</p>