In this study we explore the experiences of new teachers in urban schools at the intersection of three major policy agendas--alternative certification, new teacher retention, and the small schools movement. We examine alternatively certified teachers' perceptions of the rewards and challenges of teaching in small schools, the support neophyte teachers seek and receive in these unique educational settings, and the reality of small school implementation in a modern urban environment. The findings have implications for policy-makers, urban school reformers, teacher educators and professional developers, administrators and teachers working to create and implement effective policy for twenty-first century urban schools.