Today’s educational environment has made it more difficult to rely on the Halstedian model of “see one, do one, teach one” in gynecologic surgical training. There is decreased surgical volume, but an increased number of surgical modalities. Fortunately, surgical simulation has evolved to fill the educational void. Whether it is through skill generalization or skill transfer, surgical simulation has shifted learning from the operating room back to the classroom. This article explores the principles of surgical education and ways to introduce simulation as an adjunct to residency training. We review high- and low-fidelity surgical simulators, discuss the progression of surgical skills, and provide options for skills competency assessment. Time and money are major hurdles when designing a simulation curriculum, but low-fidelity models, intradepartmental cost sharing, and utilizing local experts for simulation proctoring can aid in developing a simulation program.