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The aim of the study was to (1) assess differences in how male and female general surgery residents utilize duty-hour regulations and experience aspects of burnout and psychological well-being, and (2) to explore reasons why these differing experiences exist.There may be differences in how women and men enter, experience, and leave residency programs.A total of 7395 residents completed a survey (response rate = 99%). Logistic regression models were developed to examine the association between gender and resident outcomes. Semistructured interviews were conducted with 42 faculty and 56 residents. Transcripts were analyzed thematically using a constant comparative approach.Female residents reported more frequently staying in the hospital >28 hours or working >80 hours in a week (≥3 times in a month, P < 0.001) and more frequently feeling fatigued and burned out from their work (P < 0.001), but less frequently “treating patients as impersonal objects” or “not caring what happens” to them (P < 0.001). Women reported more often having experienced many aspects of poor psychological well-being such as feeling unhappy and depressed or thinking of themselves as worthless (P < 0.01). In adjusted analyses, associations remained significant. Themes identified in the qualitative analysis as possible contributory factors to gender differences include a lack of female mentorship/leadership, dual-role responsibilities, gender blindness, and differing pressures and approaches to patient care.Female residents report working more, experiencing certain aspects of burnout more frequently, and having poorer psychological well-being. Qualitative themes provide insights into possible cultural and programmatic shifts to address the concerns for female residents.