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Background: Resident attrition is costly but literature studying the motivations behind it in obstetrics and gynaecology (OBGYN) is lacking. Objectives: We aimed to study the relationship between prior specialty-appropriate work experience and risk of attrition amongst OBGYN residents in Singapore, and identify factors placing residents at greater risk of attrition. Methods: This nationwide mixed methods case control study studied all OBGYN residents in Singapore for the 2011 and 2012 intakes. A pre-piloted questionnaire was used to identify work experience and risk factors related to resident attrition. Structured interviews were conducted with a subgroup of participants chosen for diversity of educational background, work experience, and position towards residency. Results: 28 of 33 (84.8%) eligible residents participated in this study. Female (40.9% vs. 0%), married (50.0% vs. 22.2%) and Singaporean (38.1% vs.14.3%) residents more often considered attrition from training. Those accepted into residency after graduation were 33% less likely to have considered leaving. No statistical difference was observed between residents with prior work experience and those without (38.9% vs. 20.0%, p=0.417). All interviewees believed that prior experience informs expectations and eases initial learning. Low job satisfaction related to mismatched expectations was the most quoted reason for considering attrition. 85.7% of interviewed residents were concerned about competing work and family demands. Conclusions: Lack of specialty-appropriate work experience contributes to misinformed training expectations and increased attrition risk. Residents who have considered attrition may still desire career longevity in their specialty. Reduction in mismatched expectations promises to improve job satisfaction and translate to career longevity.