The transition from medical school to residency in the United States consumes large amounts of time for students and educators in undergraduate and graduate medical education (UME, GME), and it is costly for both students and institutions. Attempts to improve the residency application and Match processes have been insufficient to counteract the very large number of applications to programs. To address these challenges, the Coalition for Physician Accountability (CoPA) charged the Undergraduate to Graduate Review Committee (UGRC) with crafting recommendations to improve the system for the UME-GME transition. To guide this work, the UGRC defined and sought stakeholder input on a “blue-skies” ideal state of this transition. The ideal state views the transition as a system to support a continuum of professional development and learning, thus serving learners, educators, and the public, and engendering trust among them. It also supports the well-being of learners and educators, promotes diversity, and minimizes bias. This manuscript uses polarity thinking to analyze 3 persistent key tensions in the system that require ongoing management. First, the formative purpose of assessment for learning and growth is at odds with the use of assessment data for ranking and sorting candidates. Second, the function of residents as learners can conflict with their role as workers contributing service to health care systems. Third, the current residency Match process can position the desire for individual choice—among students and their programs—against the workforce needs of the profession and the public. This Scholarly Perspective presents strategies to balance the upsides and downsides inherent to these tensions. By articulating the ideal state of the UME-GME transition and anticipating tensions, educators and educational organizations can be better positioned to implement UGRC recommendations to improve the transition system.