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Introduction: Increasingly medical students pursue medical education abroad. Graduates from International Medical Programs (IMPs) practice globally, yet how to prepare students for an unknown international environment is complex. Following IMP graduates throughout their early careers, this study offers insights into gaps in current undergraduate education. Methods: In this international, longitudinal, mixed-methods study, 188 graduates from seven IMPs completed baseline surveys on career choice and job preparedness. Forty-two participants completed follow-up until three years after graduation. Nine graduates participated in semi-structured interviews on individual experiences and the evolution of their perspectives. The multiphase, sequential design allowed data collected at baseline to inform further data collection instruments. Results: Two typical student profiles emerged. The first depicts a student who, despite the challenges of studying abroad, pursues a medical degree ‘anyhow’, with a common aim of practicing in their home country. The other deliberately selects an IMP while envisaging an international career. Two years after graduation, the majority (> 70%) of our participants were practicing in a country other than their country of training. They reported challenges around licensing, the job application process and health system familiarization. Participants’ experiences point towards potential curriculum adaptations to facilitate cross-border transitions, including career guidance, networking and entrance exam preparation. Discussion: IMP graduates lack support in practical aspects of career orientation and international exposure. Most IMPs essentially prepare their graduates for a career elsewhere. Gaps and challenges that IMP graduates experience in this cross-border career transition entail a responsibility for preparation and guidance that is currently lacking in IMP curricula.