Interorganizational cooperative relationships offer the potential to develop high quality, low cost information systems. Yet, such relationships are conspicuous by their absence, and important theoretical issues remain to be examined. In this paper, we analyze three cases of cooperative development of information systems, using the frameworks of cooperation theory and configuration theory. Cooperation theory highlights the role of trust in cooperation whereas configuration theory highlights the role of configurational compatibility. The within-case and cross-case analysis finds the pattern of cooperation to be paradoxical within the framework of cooperation theory, but, consistent with configuration theory, cooperation fell with increasing configurational distance. We find that the organizational changes required to overcome small configurational distances are complex and difficult to implement, raising barriers to cooperation. We examine the implications of configurational distance for the adoption and implementation of information systems innovations and suggest that configurational distance is a useful contingency variable in implementation research.