How do we ensure a high-quality education for all K-12 students in the United States, especially in urban settings where there are generally fewer experienced teachers and greater difficulty in attracting and retaining highly trained teachers? How do we work to diversify the teacher workforce to better reflect demographics of children in classrooms? In recent years, many states like California have come to rely on underprepared teachers (i.e., those without a preliminary credential) to help fill critical teacher shortages. The number of new teachers entering California’s classrooms via these pathways has grown rapidly while enrollment in teacher preparation programs has declined according to California’s Commission on Teacher Credentialing data. One potential solution involves urban teacher residency (UTR) programs that provide innovative approaches to the recruitment, preparation, and retention of new teachers in high-need urban schools. In UTR programs, teachers are prepared to work in an urban context and to develop competencies that will enable them to be successful when and where they are most needed. This chapter explores evaluation findings from a UTR program in California and efforts to gather more systematic data drawn from state agencies to follow new teachers entering the profession via different pathways over time.