Although pregnancy during surgical residency is increasingly common, studies of surgical residents have identified challenges associated with pregnancy and motherhood. These include perceptions of different maternity leave policies among institutions, lack of mentorship, stigma, and desire for greater lactation support. To describe the perspective and experience of US surgical program directors regarding maternity leave and postpartum support for surgical residents. This qualitative study included surgical program directors of US general surgery residency programs who were selected using purposive-stratified, criterion-based sampling. Transcripts were collected from semi-structured interviews, which were audio-recorded and transcribed verbatim, from October 21, 2018, to June 1, 2019. Maternity leave and postpartum support. Perspectives of program directors regarding maternity leave and postpartum support were categorized into common themes identified using content analysis. A total of 40 US general surgical programs directors (28 [70.0%] male; mean [SD] age, 49.7 [6.8] years) were interviewed, of whom 36 (90.0%) were from university-based programs. All reported having maternity leave policies allowing a duration of leave of 6 weeks or longer. Analysis of program director interviews identified 5 themes: (1) residents are reluctant to extend training despite being offered multiple leave options; (2) childbearing negatively impacts the quality of work of certain residents; (3) lack of formal lactation policies creates practical challenges in supporting residents who are nursing; (4) resentment from coresidents who are asked to provide maternity leave coverage varies based on the prepregnancy reputation of the resident on leave; and (5) lack of salary support limits the practicality of extended leave options. Complex interpersonal issues affected residents differently, including stigma, reluctance to change established surgical training patterns, and challenges with work-life balance. This qualitative study found that sociopolitical issues within surgical training culture and fiscal constraints created obstacles against program directors supporting pregnant residents. These findings suggest that a multidimensional approach to supporting residents through written maternity and lactation policies, structured mentorship and coaching programs, and efforts by leadership to enforce family priorities is needed to promote a surgical culture that normalizes pregnancy and motherhood during training.