Purpose: Urban school districts often face challenges in filling principal vacancies with effective leaders, especially in high-needs schools. Prospective principals' engagement with the job application process may contribute to these challenges. The goal of this study is to better understand the job search strategies and behaviors of prospective principals and how their approaches might contribute to leadership staffing challenges in high-needs schools. Research Design and Methods: We employ a convergent mixed-methods design that draws on data from two urban school systems. We pair analysis of interviews of 36 principals who have recently navigated the districts' hiring systems with multiple years of applications and other administrative data provided by the two districts. We explored how patterns and themes that emerged from each data source were confirmed or disconfirmed with the other source. Findings: Guided by a job-search model, our analysis uncovers three main findings. First, the typical principal applicant conducted a targeted rather than a wide search, reflecting multiple strategies, preferences, and relational factors. Second, elementary educators showed a strong propensity to apply to the same grade level. Third, leaders applied to schools serving larger proportions of historically marginalized students at similar rates as other schools, reflecting their motivations to work with underserved students. Implications for Research and Practice: Considerations informing prospective principals' job searches are multifaceted. High-needs schools are desirable to many principal candidates. Identifying and strategically recruiting candidates with preferences for working in such schools can be a strategy for districts seeking to overcome challenges in filling principal vacancies.