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Background and Objectives: The Undergraduate Medical Education for the 21st Century (UME-21) project encouraged the formation or enhancement of partnerships between medical schools and health care organizations distinct from the traditional teaching hospitals. The purpose was to prepare medical students in nine content areas that were components of the UME-21 project. Despite their importance today to medical schools, such partnerships with health care organizations are a challenge to develop and maintain in the midst of a rapidly changing health care environment. This article categorizes the partnerships formed and discusses the benefits and the barriers encountered in such collaborations., Methods: Information about the partnerships was abstracted from written reports from each of the UME-21 partner schools. Additional information was obtained from personal communications with external project representatives and from a post-project survey presented to all UME-21 partner schools., Results: The eight partner schools established or enhanced 32 educational partnerships with external organizations. External partner organizations contributed to curriculum planning and implementation, course development and presentation, and provision of clinical sites and preceptors. Twenty-seven of 32 initial affiliations continued in some form beyond the contract period., Conclusions: Partnerships formed as part of the UME-21 project improved medical students' exposure to the health care system and their knowledge and skills for effective practice in the 21st century health system. Barriers encountered included financial pressures, changes in leadership, different organizational missions and priorities, and preexisting prejudices against new relationships. Factors associated with successful partnerships include the presence of a health care organization and an academic "champion" dedicated to the project, strong individual relationships, and a medical school commitment to involve external partners.