Introduction: There has been a notable worldwide rise in the percentage of women delivering via cesarean section. Although cesarean section is generally considered safe, there is a possibility of significant health risks and even mortality associated with it. The aim of this study was to collect pertinent data on the perspectives of healthcare providers, particularly obstetricians, who are involved in the field of labor and delivery in Greece, regarding the choice of Trial Of Labor After Cesarean (TOLAC). Material and Methods: This was a cross-sectional study, conducted at the Third Department of Obstetrics and Gynecology, School of Medicine, Faculty of Health Sciences, Aristotle University of Thessaloniki, Greece; obstetricians were interviewed via certain questionnaires. Detailed analysis of the different characteristics regarding obstetricians’ background, workplace, preferences, willingness to take risks and safety concerns was conducted. These variables were compared and correlation between them was thoroughly investigated. Results: In total, 333 responses to the questionnaire were collected through Google online forms. Few obstetricians seem to enjoy taking risks, while most of them are neutral and willing to perform a planned TOLAC. It seems that as the experience of obstetricians increases, their tendency to recommend TOLAC on their own does not increase. The majority of obstetricians who had a failed TOLAC were more negative than those who had not had a failed attempt; whereas, they were willing to undertake TOLAC when the time required to transfer the women from the labor ward to the operating table was the minimum possible. Concerning the security as an important element in every aspect of obstetricians’ lives, the majority of them responded neutrally or positively. Following gender analysis, results showed that both male and female obstetricians were neutral or would avoid situations that have an uncertain outcome. Conclusion: Obstetricians and healthcare providers are willing to offer TOLAC as an option, provided that certain criteria are met and safety considerations are addressed. Finally, the acceptance and practice of TOLAC may vary between different regions, hospitals and individual healthcare providers.