Objective <p>To assess demographics, educational backgrounds, initial challenges, professional interests, and attitudes towards post-residency MD training among Oral and Maxillofacial Surgery (OMS) residents in Israel.</p> Methods <p>Cross-sectional survey of 57 active OMS residents across all 9 accredited programs in Israel (June-October 2021). The questionnaire addressed demographics, educational&#xa0;background, residency experiences, challenges, professional interests, and future plans.</p> Results <p>Mean age was 34.6 years (67% male). Most (75.5%) graduated from Israeli dental schools, contrasting sharply with the general dental workforce (26% domestic graduates, <i>P</i> &lt; 0.001). Primary challenges included adapting to hospital work demands (56.1%) and feeling overwhelmed by OMS knowledge requirements (54.4%). Residents with initial medical rotations reported significantly better adaptation (<i>P</i> = 0.047). Mediation analysis revealed that medical rotations improve adaptation partially through delayed overnight shift commencement. Trauma (63.2%), orthognathic surgery (52.6%), and oncologic surgery (35.1%) were areas of highest interest. Confidence in complex procedures increased significantly with training progression (<i>P</i> &lt; 0.05). One-third planned post-residency MD training, with research degree holders more likely to pursue this path (OR = 2.76, <i>P</i> = 0.024).</p> Conclusions <p>This study highlights improvement opportunities in Israeli OMS residency training, particularly structured early medical training and tailored support for international graduates.</p>