The practice of ultrasound is an art that requires complex cognitive and behavioral skills that are acquired following sustained practice. Performance needs to satisfy standards that are set by professional organizations and learned societies. Failure to reach these standards results in suboptimal patient care, if not harm and medicolegal consequences. In this chapter, the authors (1) review the current standards for practice in gynecology and assisted reproduction set by leading organizations, (2) outline the learning and teaching models for skill acquisition, (3) ascertain when and where simulation and other interventions might be implemented to support learners’ acquisition of ultrasound skills, and (4) explore the timing and methods of assessment that enable learners to demonstrate competency and set them on the path of proficiency, hence reassuring the public.