Background: Lack of surgical apprenticeship caused by the COVID-19 pandedmic has limited learners preparation for residency and may impair their psychomotor competence. Using virtual reality simulation and videotelephony technology, we designed a telementoring opportunity for medical students interested in surgery to receive expert coaching for technical skill acquisition. The following report outlines this innovative approach and investigates its effectiveness. Methods: In a 3-week workshop, senior neurosurgery residents were trained to teach brain tumour resection techniques using the Objective Structured Assessment of Technical Skills (OSATS) rating scale and the Promoting Excellence And Reflective Learning in Simulation (PEARLS) debriefing guide for assessment and feedback, respectively. Medical students were recruited to participate in neurosurgical simulation training. Participants performed 5 tumour resections for practice and 1 complex tumour resection for skill evaluation. The intervention's effectiveness was measured and compared with a no-feedback control grroup using the final resection's blinded OSATS rating in a randomized controlled trial. Results: Good interrater reliability (intraclass correlation coefficient = 0.84) was achieved, and the OSATS scale demonstrated good internal consistency (a = 0.82). Forty-seven medical students from 4 institutions were randomly assigned to instructor (n = 23) and control (n = 23) groups. In the instructor group, live on-screen performance of participants was assessed remotely with verbal debriefing provided upon completion of each practice resection. No performance assessment or feedback was provided to the control group. Blinded OSATS assessment showed that instructor feedback significantly enhanced respect for tissue (p = 0.027), economy of movement (p = 0.024), and instrument handling (p = 0.012). Conclusion: Residents were engaged in providing effective assessment and feedback in remote-based simulation training for undergraduate medical students.