Background: Enrollment into Oral and Maxillofacial Surgery (OMFS) in Saudi Arabia is low generally. Aim: To evaluate the reasons guiding the choice of OMFS as a specialty by final year dental students and interns. Methodology: A questionnaire-based cross-sectional survey among final year students and interns across major Dental Colleges in Saudi Arabia. Respondents were asked to provide information regarding demographics, level of training, interest in specialty training, intended areas of specialization and factors influencing choice of OMFS or not. Results: In total, 210 questionnaires were returned. Out of these, 139 (66%) were final year students and 71(34%) interns; 112 (53%) were men and 98 (47%) were women; and most of them 189 (90%) were in 21–25 years age range. Overall, 209 (99.5%) were interested in specialty training. Knowledge of the scope of OMFS ranged from 73%-90% and 50% were interested in OMFS. Main motivation for interest was “desire to be a surgeon” (n=71, 34%). “Preference for other specialties” was the reason for lack of interest in OMFS (41%) and another 32% said that “long hours of surgeries and night calls” was their reason. Conclusions: Interest in postgraduate training was very high. The respondents demonstrated a good knowledge of OMFS and interest in the specialty also. Desire to be surgeon was the main motivating factor whereas preference for other specialties and the demands of OMFS in terms of the long hours in OR and night calls were reasons for lack of interest in the specialty.