In this article, James Noonan uses portraiture to examine how the administrative team and the teachers at a small, urban middle school approach school improvement. He illustrates the ways in which the pressures associated with attempting school reform in our current high-accountability environment make it difficult for school personnel to engage in the deep learning that transformative change requires. Noonan finds that at Fields Middle School, district-initiated redesign is built around an expansive view of learning that embraces uncertainty, collaboration, and reflection as catalysts for broad and sustained school improvement. He illuminates school transformation efforts that hinge on adult learning and an understanding of schools as learning organizations, in contrast to reform efforts that adopt linear and hierarchical views of teaching and learning.