Purpose: We adapted the Pomodoro study method, a structured time-management strategy recommended for medical students, into a rapid-cycle upper extremity and neck workshop, using small-group skill stations, a train-the-trainer model for facilitator development, and a reverse demonstration design in which students attempted maneuvers before faculty demonstration. The workshop was developed to address a curricular gap in musculoskeletal instruction during clerkship while promoting learner engagement. Methods: The three-hour workshop consisted of five upper extremity and neck blocks with four six-minute stations in which students first attempted maneuvers with coaching by a facilitator before observing faculty demonstration. Fifty-six third-year medical students rotated in groups of 3-4 through the stations. Twenty-three facilitators participated in a train-the-trainer model using standardized training materials (objectives, exam benchmarks, teaching tips, anatomy diagrams, and videos) to promote consistent instruction and resident educator development. Stations emphasized repeated hands-on practice with immediate feedback. Facilitators and students completed post-workshop surveys. Results: Survey responses indicated strong support for the fast pace and extensive hands-on practice. Students reported that the reverse demonstration format improved understanding and confidence. Most felt the timing kept them engaged, though many suggested extending stations by one to two minutes. Facilitators reported that the train-the-trainer materials improved preparation and promoted more consistent instruction. Conclusions: Pomodoro-inspired microlearning which mirrors student study habits, reverse demonstration, and a train-the-trainer framework created an engaging model that promoted learner confidence and facilitator development. A complementary lower extremity workshop is planned for later this year.