Background: Reflection on the process of learning is an essential ingredient in transforming novice into expert learners. Learning to compile portfolio encourages reflective skills, which help students to work systemically in translating metacognition into self-regulatory control in order to adjust their action and monitor their learning objectives. Introducing to compile portfolio in the early years of postgraduate training is an effective tool to stimulate students’ reflective abilities. Reflective learners are better motivated than the conventional learners to take the responsibilities as researcher in future. Reflective skills achieve both learning in right direction and learning for whole life. However, use of formal methods of reflective portfolio to monitor the learning objectives is an uncommon practice in postgraduate training, primarily due to intensive time and labor required. Challenged with those constraints in Master’s of Surgery Program of Otolaryngology and Head-Neck Surgery in School of Medical Sciences at Universiti Sains Malaysia, a structured self-reflective portfolio was introduced to determine its feasibility and acceptance among supervisors and trainees. Portfolio was practiced as one of the tool for formative assessment and for making recommendations to certify independent thyroid surgery allowed to practice in future. Methodology: A self-reflective structured portfolio was introduced to monitor the learning objectives in trainees of 2007 cohort, using a model as "mentor-system for authentic and structured learning with self-reflective assessment" (MASSRA). Initially a semi-structured portfolio comprising of 12 items and guidelines to compile a portfolio was followed by a structured format in training of thyroid module in sub-specialty of Head and Neck Surgery. Mentoring was organized by putting one-mentor verses 9 students to provide general pastoral guidance to compile portfolio as two entries a year. Mentors held the counseling session with student twice a year after evaluating the portfolios to monitor their progress. Besides, candidates were also observed for their performance in thyroid surgery during a 4-years training program. Those identified with problems for their level of training were referred to "Joint Committee for Surgical Training" comprising of 3 supervisors from Head and Neck Surgery Sub-specialty and a chairman supposedly the head of the department. 7 randomly selected students were also interviewed for direct feedback to evaluate this model. Result: 28 trainees at different level of their training compiled a self-reflection structured portfolio minimum twice a year with instructional feedback from the mentor, which was used as a tract for their personal development plan (produced by each trainee) for training in thyroid surgery. Initial analysis of portfolio revealed interesting feedback from the trainees reflecting on their knowledge, surgical skills and attitude towards thyroid surgery seen in tables 2-4. Conclusion: Self-reflections about each structured items in portfolio-helped trainees to identify their problems, seek mentors guidance and work systemically to help adjust their actions by revising learning objectives. Though time and labor intensive, portfolio was rated as feasible and practical.