Background: Longitudinal standardized patient (LSP) experiences mimic clinical practice by allowing students to interact with standardized patients (SPs) over time. LSP cases facilitate practice, assessment, and feedback in clinical skills and foster an appreciation for the continuum of care.Objective: We sought to characterize the nature of relationship-building, feedback, and continuity among all stakeholders participating in a single LSP program.Design: We developed and implemented a novel LSP program. Students encountered two LSP characters six times each during the first 2 years of medical school, though continuity pairings of students, SPs, and faculty were frequently not possible. Focus groups were held with second-year medical students (N = 15), core faculty who coached these students in LSP encounters (N = 8), and SPs who had played the role of either LSP character (N = 10) participated. Results were analyzed thematically using a template analysis approach.Results: The longitudinal nature of the experience reinforced the importance of student growth over time, the key role of faculty and SPs in providing feedback, and the tension between feedback and assessment. Students reported that LSP cases encouraged practice and feedback. SPs felt wedded to the longitudinal characters. Continuity pairings were recommended by all stakeholders to increase authenticity and promote relationship-building.Conclusion: Stakeholders observed that the LSP cases brought some sense of continuity missing in other clinical skills encounters which helped prepare students for patient care. Continuity pairings of students, faculty, and SPs were recommended to enhance relationship-building and feedback.