Objective To assess the behavior and preferred delivery method among Iranian obstetricians in challenging cases. Method Using the revised Jackson personality inventory questionnaire, the attitudes of obstetricians toward cesarean delivery were assessed in challenging childbirth cases. The study was conducted at the Mashhad University of Medical Sciences in Mashhad, Iran. Result Seventy-five obstetricians answered each item reflecting varying levels of preference and risk attitudes. However, a significant number of respondents avoided the risk of requesting a cesarean because of legislation and legal issues. Conclusion Iranian obstetricians prefer low-risk behavior for managing ambiguous delivery cases. Fear of legislation and medicolegal issues appear to be of great importance in this cohort primarily comprising female physicians.