Faced with the remarkable absence of thoughtfulness in U.S. classrooms, some proponents of school restructuring have argued that innovative organizational structures are needed to assist teachers in their efforts to improve the thoughtfulness of classroom practice. Building on previous studies of the general relationship between organizational features and the promotion of classroom thoughtfulness, this analysis presents an in-depth analysis of four secondary social studies departments that made structural changes in school organization while also placing an emphasis on promoting higher order thinking. This analysis suggests that although innovative organizational structures in and of themselves are generally not associated with higher levels of classroom thoughtfulness, innovative organizational structures, in specific contexts, have been positively associated with classroom thoughtfulness. Among the four departments studied here, certain organizational structures, when combined with clear curricular emphases, did appear to be associated with higher levels of classroom thoughtfulness.