In light of the COVID-19 pandemic in 2020, United States Medical Licensure Examinations (USMLE) announced its momentary cancellation of its Step 2 Clinical Skills (CS) Examination. This suspension brought to attention the need to evaluate the current methods of clinical skills assessment. Objectively, this period in medical education marks a time for change and improvement. Although this may seem radical, medical education has been continuously changing over the past few decades. The utilization of long case, short case, and viva voce examinations for clinical skills assessment morphed into using the Objective Structured Clinical Examination (OSCE) and Step 2 CS. While OSCEs and Step 2 CS are currently mainstay assessment methods in medical education, the new challenges that COVID-19 has imposed requires medical educators to improve these methods in order to maintain social distancing guidelines. Special consideration should be made to incorporating modalities such as video conferencing, artificial intelligence, virtual reality, and workplace based assessments. The momentary suspension of medical school activities was clearly unexpected, but it is vital that medical educators continue to improve clinical skills assessment in conjunction with the present times.