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Introduction: COVID-19 altered the landscape of medical education, disrupting the general surgery residency application process. Decreased access to clinical rotations, limited access to in-person mentors, and lack of in-person interviews, highlighted the need for mentorship programs. We examined the impact of virtual mentoring following the implementation of a novel program for trainees entering the field of general surgery. Methods: We designed an exclusively online virtual mentoring program that focused on an individualized, tailored approach in five domains: requesting letters of support, personal statement composition, resume editing, interview skills, and residency program ranking. Immediately following completion of the program, a nineteen-question electronic survey was administered. Results: 18 out of 19 participants completed the survey. Following the completion of the program participants were more confident in all five domains targeted by the program when responding to survey stems (5-point Likert scale (5-strongly agree)). Utility of the program, likelihood to recommend, and likelihood to participate again in virtual mentoring were all positive 5 [4-5]. Respondents reported less concern about the impact of COVID-19 on the application cycle. Trainees reported that virtual mentoring is likely to play an increasingly important role in training programs 5[4-5]. Participants also reported an increased confidence in the match, with a pre-program median of 67 [50 - 65] and post-program median of 84 [75-91] (0.004). Conclusion: Virtual mentoring tailored for medical students entering the match is well received and increases participant confidence. This data should be used as a framework to expand and develop virtual mentoring programs.