Transition to residency (TTR) courses help alleviate medical students' concerns about preparing for residency; however, existing TTR courses are often limited to teaching clinical or procedural skills without addressing the nonclinical skills necessary for transitioning to practice. This report describes the use of design thinking (DT) to develop a learner-centered TTR course at the State University of New York Downstate Health Sciences University. DT consists of 5 steps: discovery, interpretation, ideation, experimentation, and evolution. The first 3 steps were used for needs assessments and course design. During the discovery step, empathetic, semistructured interviews of interns, program directors, and graduating medical students were conducted to identify concerns about starting residency. During the interpretation step, thematic analysis of interviews was performed to identify areas of concerning attitudes and deficient skills and to inform content. In the ideation step, a 2-week curriculum was designed, including didactic lectures, small group discussions and workshops, simulation, and procedure labs, to address the defined content areas. During the fourth step, implementation, a 2-week pilot elective course of the designed curriculum was conducted in spring 2021 with 6 students. Participant feedback from 2 students collected 6 months into internship found the procedures and simulated clinical skills cases high yield, appropriate, relevant to intern practice, and valuable. The course size in spring 2022 increased to 19 students, and the curriculum was refined based on the feedback of the previous pilot course (from 2 students and 4 faculty members) and from a precourse student survey (5 students). The last step of DT, evolution, included determining larger-scale feasibility while maintaining learner-centeredness and conducting a programmatic evaluation. The iterative, adaptable approach of DT is suitable for TTR design and is generalizable. Other institutions can adapt the DT approach to develop their own institutional TTR programs.