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The majority of analysis on teacher retention and turnover relies on quantitative data. Drawing on interviews with practicing teachers who graduated from a Teacher Residency program connected to a large private university in the Northeast, this study analyzes teacher turnover and retention through a qualitative lens. By looking deeply into the reasons behind teachers' decisions to stay, move, or leave- in their own words- especially those in urban, under-resourced schools, we can begin to understand how to positively impact teacher retention through the organization of teacher education programs, school administrations, and local and state policies.