Using focus group and interview data collected annually over four years with participants in an alternative-route school leadership preparation program, we examine the strengths and challenges of the preparation model as implemented in a small urban district. Representing a partnership between the city school district, local charter school networks, and a large nonprofit organization, the program provided a two-year residency for aspiring administrators working as assistant-level administrators or teacher leaders. By their second program year, most residents reported feeling rigorously prepared for school leadership roles. Amid declining enrollments and school closures, residents' career paths diverged over time, with two of 42 initially placed residents obtaining principalships within the four-year study period, and about a third receiving promotions to higher positions. Residents reported differing levels of support for their residency roles, especially those teachers in instructional leadership roles. Some program participants reported that residents in their schools were strategically deployed to distribute responsibility for instructional improvement; this was particularly true in schools staffed by program alumni.