This qualitative case study examined the organizational learning mechanisms utilized by a district superintendent and their impact on principals’ learning. Examining recent curriculum reform efforts, the study concentrated on a small sample of building principals within a mid-sized urban public school district. Grounded in both organizational and situated learning theories, the research focused on organizational learning mechanisms and the interplay created by their implementation through the analysis of interview data and documents. Findings highlighted how the superintendent interpreted and distributed information to principals. In addition, findings showed the impact that superintendent-initiated processes, behaviors, and structures had on principal learning. The study provided strong evidence that the superintendent under study took steps to create district structures to support organizational learning. Moreover, principal data showed the impact of these structures on principals’ perceived learning.