To increase the supply of teachers into underserved schools, teacher educators and policymakers commonly use two approaches: (a) recruit individuals who already report strong preferences to work in underserved schools or (b) design pre-service preparation to increase preferences. Using survey and administrative data on more than 1,000 teachers in a large, urban district, this study provides some of the first district-level evidence for both approaches. Individuals with stronger underserved preferences and teachers of color were more likely to enter underserved schools. Underserved preferences also increased across pre-service student teaching, although increases were mostly unrelated to working with underserved student populations.