This is an interpretive case study of two school systems that implemented an integrated curriculum and administrative information system. Rogers’ Innovation Process in Organizations was used as a conceptual model for understanding information systems implementation. During the redefining/restructuring stage of the innovation process, issues that emerged were identified when the schools tried to create a fit between the new information system and their organization. Major findings were that 1) a poor match between the capabilities of an information system and the needs of the organization make redefining/restructuring difficult or not possible, 2) An information system that has not been tested is a challenge to full implementation, and 3) the organizational structure of the implementation needs to be adapted to each organizations technological abilities. From the findings, the author proposed a conceptual model that identifies information systems and school needs on two axes-administration and curriculum. The model would allow schools to better match their needs with prospective information systems.