The principal internship is a crucial component of principal preparation programs (PPP) in the U.S. and, increasingly, in other countries. The purpose of this study was to compare the experiences and work of principal candidates enrolled in one principal residency program (PRP) to candidates enrolled in a traditional principal preparation program at the same university. Using an embedded case study design, we collected survey, log, and interview data from interns enrolled in two different programs at one university across two semesters. We analyzed the quantitative data using descriptive statistics and iterative rounds of coding to analyze the interview and log data. Our findings suggest that the interns in both groups had a wide variety of authentic leadership experiences but that the residents had higher levels of engagement than did the traditional interns. Our findings add to our understanding of the depth and quality of interns' leadership experiences and how program structures may shape those experiences. We conclude with recommendations for principal preparation programs.