Background: Given the concurrence of medical residency and fellowship training with typical childbearing years, trainees often must make difficult decisions regarding family planning, requiring the support of their residency and fellowship program directors (PDs) to guide them. Objective: Our hypothesis was that PDs have knowledge gaps and varying levels of support in terms of their trainees' fertility, and the goal of our study was to assess the knowledge and support of residency and fellowship PDs in the United States toward trainees' reproductive needs. Methods: Cross-sectional survey distributed to all residency and fellowship PDs providing contact information through the Accreditation Council for Graduate Medical Education website in August 2019. Results: Of 299 respondents, the most common lengths of leave reported were 6-8 weeks of maternity leave and under 2 weeks of paternity leave. A total of 57.2% did not know their program's insurance for infertility treatment, and 68.6% did not know fertility preservation coverage. A total of 52.2% of PDs were unaware of if their trainees faced infertility. PDs supported residents' needs through moral support (68.2%) and time off for appointments (65.2%). Similarly, most PDs (66.2%) never had a trainee express interest in fertility preservation to them but offered moral support (59.2%) and time off (48.5%). Respondents felt it was important to increase resources for trainees by increasing their awareness of needs (47.5%) and establishing reproduction-related policies (34.1%). Conclusion: The study found variations regarding PDs' knowledge and support levels for trainees' fertility needs. Most were unaware of their trainees' fertility needs, and many PDs felt it would be important to improve resources by increasing personal awareness and creating policies for support to promote reproductive health equity for trainees.