Unlabelled: A significant component of Canadian medical education is the development of clinical skills. The medical educational curriculum assesses these skills through an objective structured clinical examination (OSCE). This OSCE assesses skills imperative to good clinical practice, such as patient communication, clinical decision-making, and medical knowledge. Despite the widespread implementation of this examination across all academic settings, few preparatory resources exist that cater specifically to Canadian medical students. MonkeyJacket is a novel, open-access, web-based application, built with the goal of providing medical students with an accessible and representative tool for clinical skill development for the OSCE and clinical settings. This viewpoint paper presents the development of the MonkeyJacket application and its potential to assist medical students in preparation for clinical examinations and practical settings. Limited resources exist that are web-based; accessible in terms of cost; specific to the Medical Council of Canada (MCC); and, most importantly, scalable in nature. The goal of this research study was to thoroughly describe the potential utility of the application, particularly its capacity to provide practice and scalable formative feedback to medical students. MonkeyJacket was developed to provide Canadian medical students with the opportunity to practice their clinical examination skills and receive peer feedback by using a centralized platform. The OSCE cases included in the application were developed by using the MCC guidelines to ensure their applicability to a Canadian setting. There are currently 75 cases covering 5 specialties, including cardiology, respirology, gastroenterology, neurology, and psychiatry. The MonkeyJacket application is a web-based platform that allows medical students to practice clinical decision-making skills in real time with their peers through a synchronous platform. Through this application, students can practice patient interviewing, clinical reasoning, developing differential diagnoses, and formulating a management plan, and they can receive both qualitative feedback and quantitative feedback. Each clinical case is associated with an assessment checklist that is accessible to students after practice sessions are complete; the checklist promotes personal improvement through peer feedback. This tool provides students with relevant case stems, follow-up questions that probe for differential diagnoses and management plans, assessment checklists, and the ability to review the trend in their performance. The MonkeyJacket application provides medical students with a valuable tool that promotes clinical skill development for OSCEs and clinical settings. MonkeyJacket introduces a way for medical learners to receive feedback regarding patient interviewing and clinical reasoning skills that is both formative and scalable in nature, in addition to promoting interinstitutional learning. The widespread use of this application can increase the practice of and feedback on clinical skills among medical learners. This will not only benefit the learner; more importantly, it can provide downstream benefits for the most valuable stakeholder in medicine-the patient., (© Ayma Aqib, Faiha Fareez, Elnaz Assadpour, Tubba Babar, Andrew Kokavec, Edward Wang, Thomas Lo, Jean-Paul Lam, Christopher Smith. Originally published in JMIR Medical Education (https://mededu.jmir.org).)