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The primary aim of this study was to investigate whether the types of postgraduate trainees’ teaching barriers would be associated with their experience levels and the four clinical settings in Obstetrics and Gynecology (OB/GYN). Individual semi-structured interviews with 13 OB/GYN residents and Fellows were conducted and followed by an online survey sent to all OB/GYN residents and Fellows in three research sites. Descriptive statistical analysis and thematic analysis were applied. Eleven OB/GYN residents and two Fellows participated in the interviews. Of 93 possible OB/GYN resident and Fellow respondents, 57 (61.3 %) completed the online survey. Limited time was the predominant barrier across OB/GYN trainees’ experience levels. Six factors contributing to the teaching barriers were identified. Major types of teaching barriers perceived by trainees were similar in outpatient and labor and delivery settings, but differed from perceived barriers in the inpatient and operating room settings. Major types of teaching barriers were associated with trainees’ experience levels as well as the four clinical settings in OB/GYN. Findings from this study deepen OB/GYN clerkships and residency programs’ understanding of Trainee-as-Teacher, as well as provide useful information for programs to manage teaching tasks and to further enhance the implementation of Trainee-as-Teacher curricula efficiency.