In response to the COVID-19 pandemic, many educational activities in general surgery residency have shifted to a virtual environment, including the American Board of Surgery (ABS) Certifying Exam. Virtual exams may become the new standard. In response, we developed an evaluation instrument, the ACES-Pro, to assess surgical trainee performance with a focus on examsmanship in virtual oral board examinations. The purpose of this study was two-fold: (1) to assess the utility and validity of the evaluation instrument, and (2) to characterize the unique components of strong examsmanship in the virtual setting, which has distinct challenges when compared to in-person examsmanship. We developed a 15-question evaluation instrument, the ACES-Pro, to assess oral board performance in the virtual environment. Nine attending surgeons viewed four pre-recorded oral board exam scenarios and scored examinees using this instrument. Evaluations were compared to assess for inter-rater reliability. Faculty were also surveyed about their experience using the instrument. Pilot evaluators found the ACES-Pro instrument easy to use and felt it appropriately captured key professionalism metrics of oral board exam performance. We found acceptable inter-rater reliability in the domains of verbal communication, non-verbal communication, and effective use of technology (Guttmann's lambda-2 were 0.796, 0.916, and 0.739, respectively). The ACES-Pro instrument is an assessment with evidence for validity as understood by Kane's framework to evaluate multiple examsmanship domains in the virtual exam setting. Examinees must consider best practices for virtual examsmanship to perform well in this environment. The online version contains supplementary material available at 10.1007/s44186-023-00107-7.