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This descriptive single case study foregrounded teacher-based policy analyses of the Title I School Improvement Grant program. Six successful urban high school teachers analyzed the localized interpretation of the program’s Transformation and Turnaround models. Impacts on their capacity to improve student outcomes and ways in which policy interpretation/implementation impacted their understanding of school reform writ large were evaluated. The processes governing communication, delivery of teacher supports, and teacher retention were cited as having detrimental impacts teachers’ efforts to remain engaged in and confident about the school improvement plan. Teachers reported their capacity to fulfill their roles in the turnaround policy were acutely effected, both positively and negatively, by key district decisions concerning the timing and processes of policy implementation.