This case describes challenges in the adoption and implementation of IT in two public sector enterprises in the postal and distribution businesses respectively, in India. In spite of similarities in the scale of operations and the general cultural contexts, the IT adoption processes and outcomes of the two organizations were significantly different. While one failed to implement IT in its crucial processes, the other responded effectively to changes in external conditions by developing and using IT applications for critical functions. The case illustrates how differences in organizational factors such as top management commitment, unions, middle management participation, capabilities of IS professionals and specific aspects of organization culture resulted in such differences. The case is interesting and significant because it is representative of experiences of many government-aided organizations in India, which have undertaken IT modernization as a response to external changes and government mandates. The findings can also be generalized across similar organizations in other developing countries.