Transitions are both a blessing and a curse for learning and professional development. While transitions can afford valuable opportunities for growth, they can also burden learners in ways that stymie performance and development. In this Invited Commentary, the author focuses on the transition from medical school to residency—a transition that many believe has tipped too far toward burden. The commentary explores three ways of problematizing the transition to residency. The first is as a transaction problem involving a complex exchange of information among programs and people. The second is as a transfer problem in which learners must apply knowledge in new contexts. The third is a trajectory problem concerning each learner’s progression through medical education. The author describes current efforts aligned with each framing of the problem and discusses potential gaps in these efforts that might be addressed through an overarching framing of transitions in medical education as transformative processes. This framing may help the medical educational community think more holistically about the problems and solutions with transitions.