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Introduction Reflection is regarded as an important and essential component of healthcare professionals' education and practice. This cross-sectional study aimed to explore the levels of reflection habits of dental students and clinical and Ph D postgraduate trainees and to establish the relationship between students' reflection and their academic performance. Materials and Methods A total of 324 subjects (208 females, 56% ≥23 years of age) from King's College London Dental Institute, consisting of 281 undergraduate and 43 postgraduate trainees, responded to the invitation to participate and completed an online self-reported Reflection Questionnaire; this assesses two levels of non-reflective actions (Habitual Action and Understanding) and two levels of reflective actions (Reflection and Critical Reflection). Reflection results were compared amongst different cohorts and correlated with students' academic performance. Results Reflection Questionnaire mean scores were 10.7 for Habitual Action, 17.3 for Understanding, 17.0 for Reflection and 14.4 for Critical Reflection, with significant differences between cohorts of undergraduate students, clinical postgraduates and Ph D trainees. Reflection and Critical Reflection mean scores were higher as students climbed courses. Further, those ≥24 years of age and those with previous university degrees demonstrated higher reflective habits, whilst there was no gender difference. Additionally, the assessment programme methods correlated differently to the Reflection Questionnaire scores. Discussion The Reflection Questionnaire's internal reliability was acceptable. The most common approaches used by both students and trainees were Understanding and Reflection, whilst those with high Understanding scores also tended to have good Reflective scores. Further, multiple choice questions encouraged students to 'understand', whilst ill-defined problems, such as those from essays to clinical reasoning cases, increased this to the reflection scale. Conclusion To foster reflective thinking, tutoring should primarily be focused on younger students (≤23 years old) and those without a previous university degree. Further, a wide variety of assessment methods is suggested to stimulate different reflective constructs. [ABSTRACT FROM AUTHOR]