Background: Changes in the surgical training landscape have sparked an interest in developing new educational models anchored on entrustment assessment. We sought to optimize the validated OpTrust entrustment assessment tool by comparing ratings from short-course video reviews to previously validated intraoperative assessments. Methods: Entrustment assessment scores for video-based and 1-h (short-course) observations were compared to previously validated intraoperative assessment scores. Faculty and residents were surveyed for their perceptions related to operative observation. Results: There was a strong association between entrustment scores when comparing in-person to video-based observations (R2 = 0.76–0.84, p < 0.01) as well as short-course to full-duration observations (R2 = 0.65–0.76, p < 0.01). The majority of faculty and residents (>97%) felt observation did not negatively impact operative experience. Conclusions: Assessment of entrustment behaviors using short-course video review provides a feasible approach to intraoperative assessment. This latest application of OpTrust allows for the tool to be incorporated into surgical training programs across a variety of environments.