This paper synthesizes the findings of a six-year longitudinal retention study of more than one thousand urban educators in their first through tenth year of the profession. The educators studied were graduates of UCLA's Center X Teacher Education Program and the results of the study may be generalized to the population of well-prepared urban teachers nationwide, with one exception. Although most Center X graduates are female (79%), which is similar to national trends, the group’s ethnic and racial diversity contrasts sharply with national norms (though it reflects California’s increasing diversity). The longitudinal study consisted of a range of quantitative and qualitative studies to answer the following questions: (1) What is the effect of specialized teacher preparation on retention? (2) What is the effect of career advancement on attrition among highly-qualified urban educators? (3) What individual and school characteristics are associated with retention in high-poverty schools? This paper reports that Center X’s specialized approach to teacher education had a positive impact on workplace retention, but not role retention. If they decided to stay in teaching, Center X graduates were much more likely than similar teachers nationwide to stay put in the same school over time. This finding has important implications for the organizational stability and potential reform of urban schools. Focusing in on the issue of role retention, the paper reports that the proportion of attrition among Center X graduates due to changing roles within the field of education was 70% after eight years in the profession. Although largely hidden from policy view, the paper discusses how role changing is a form of sanctioned attrition that should be added to the landscape of teacher retention research. Finally, the paper reports findings that stand in stark contrast to a number of studies that have found teachers systematically move away from schools with low levels of achievement and high concentrations of poor children of color. The paper reports how student disadvantage along with the quality of a school’s professional learning community contributes to workplace retention in high poverty urban schools. The concluding section outlines promising policy responses for creating and sustaining urban schools where teachers are professionally respected, challenged, and supported; where they have autonomy and voice; and where they feel they can make a difference in the lives of their students.