Background/Context: There is an extensive body of research on school and student characteristics associated with teacher career decisions that has contributed greatly to our knowledge of teacher preferences. Yet this research also has a number of limitations, including a lack of attention to the sociocultural influences on teacher careers and the processes teachers use to find a job. Purpose/Objective/Research Question/Focus of Study: This article focused on the processes that teachers use to find a job and how they came to work in particular schools. In doing so, this article developed a new theoretical conception of teacher career decisions that incorporates Bourdieu's cultural reproduction theory and theories of action. Together, these frameworks highlight how teachers navigate through the hiring process using their practical understanding of how they could make the best match, rather than focusing on explicit preferences. Setting: Teacher applicants were recruited from six colleges that provide teachers to one Midwestern metropolitan area. This area was experiencing an oversupply of teachers. Population/Participants/Subjects: Participants included individuals currently completing teacher education programs and looking for their first teaching job. Research Design: Data for this article came from a mixed-methods study of teacher applicants' career decisions. The study design included a survey of 289 prospective elementary teachers and in-depth interviews with a subsample of 27 prospective elementary teachers at two points in the hiring season. Findings/Results: Teacher applicants' espoused preferences for schools were consistent with previous research, yet the data indicate that teacher applicants often contradicted these espoused preferences by the actual behavior on the job search. They did so by focusing on the district rather than the school when identifying open positions and focusing on feelings of comfort and familiarity when deciding to apply. Further, teacher applicants had few sources of information about schools and districts, which forced them to make assumptions about schools and thus reinforced perceptions of familiarity, fit, and comfort. Conclusions/Recommendations: Teacher applicants' practical understanding of the job search was informed by their social and cultural background and emphasized characteristics such as familiarity when making career decisions. Policy makers who want to improve the quality of teaching should focus on developing teachers who want to teach in hard-to-staff schools and on providing teacher applicants with access to more information about schools. Teacher educators should also consider ways to increase teacher applicants' familiarity and sense of comfort with schools serving high proportions of racial minority or low-income students.