Purpose Standardized patients/trained gynecological teaching associates (GTAs) assist with medical student training for breast and pelvic examination. We evaluated how a structured simulation-based workshop affected medical students' subsequent interactions with GTAs. Method This study was conducted in two parts. First, secondyear medical students volunteered for a simulation-based workshop prior to GTA sessions. Students completed preand postsimulation workshop questionnaires assessing their experience, knowledge, and confidence with breast and pelvic examination. GTA assessments of simulation workshop participants (G1) and nonparticipants (G2) were compared. Second, the simulation workshop was integrated into the medical student curriculum. All students completed the pre-and postsimulation workshop questionnaires; GTAs assessed student performance. Results In the pilot year, workshop participants (G1, n=43) showed significant improvement in self-assessment of knowledge (P<0.0001), preparation (P<0.0001), and confidence level (P<0.0001). The GTAs reported better performance for the breast (P=0.63) and pelvic exam (P=0.24) by G1 students than G2 (G2, n=79). The following year, significant improvement in skills (P<0.001) and confidence level (P<0.001) was noted comparing the pre-to postsimulation workshop questionnaires. Per GTA evaluations, the workshop remained effective even when administered to the whole class. Conclusion Simulation-based workshops significantly improve medical students' skills, knowledge, and confidence for breast and pelvic examinations.