Background The Accreditation Council for Graduate Medical Education expects residents to attain competency in systems-based practice by advocating for quality patient care, working in interprofessional teams, and implementing system solutions to prevent errors. Diabetes in pregnancy was identified as an area for improvement through comprehensive interdisciplinary and interprofessional care.Objective An interdisciplinary and interprofessional workshop was created by 3 regional academic institutions to improve collaborative practice, clinical knowledge, and clinical judgment of residents.Methods A workshop consisting of 4 clinical simulation stations for ultrasound assessment, glycemic control, hyperglycemic emergencies, and macrosomia complications was designed to address gaps in quality of care. Workshop participants were residents from 6 programs and students in nursing, pharmacy, and sonography. Attitude and clinical knowledge were measured preworkshop and postworkshop, and at 3-month and 6-to 7-month follow-up.Results There were increases in average clinical knowledge scores across time points from residents: 56.4% preworkshop, 64.8% postworkshop, 66.0% at 3-month follow-up, and 68.1% at 6-to 7-month follow-up. Additionally, participants reported positive attitudes toward interprofessional education and indicated high overall satisfaction.Conclusions Residents demonstrated improved knowledge and attitudes toward interprofessional training after participating in a large-scale simulation workshop focused on the care of patients with diabetes in pregnancy.