This article presents findings from a study of six schools in the Together Initiative (TI), which facilitates increased school autonomy from districts and expands teacher decision-making authority. This study aims to understand how TI’s theory of action changed structures, cultures, and agency as the concepts of site-based management and expanded teacher decision making were interpreted and implemented by district and school leaders and teachers.

Data were collected over the first 2 years of the initiative using a concurrent mixed-methods design. Field notes from more than 200 hours of observations and transcripts of 231 semistructured interviews with stakeholders were coded using the constant-comparative method. Findings from qualitative data were triangulated with annual teacher survey findings.

Implementation of TI varied across the six schools and depended greatly on school staffs’ existing relationships the district, principal support for decision-making structures, and the extent to which school cultures reflected trust and teachers were able to enact greater agency. Only two schools experienced moderate increases in site-based management and expanded teacher decision making; those that did not were missing at least one of these structural or cultural supports.

At a time when charter schools are touted as an effective reform model, this article informs policy and practice on the original charter concept—autonomous, innovative district schools. Our findings suggest that creating contexts where site-based management can flourish is far more complicated than changing structures or establishing supportive school cultures.