This paper investigated the organizational changes that were unfolded during the implementation of an OSS-based IS in the public sector of a developing country (DC) context and the ramifications of aspects of OSS and contextual matters on the process and its outcome. To do so, the study draws upon IS literature that views technological change as an emergent property of the complex interaction between ISs and organizational contexts, and the notions of organizational routines to explore the changes. The result of the interpretative case study suggests that although the license, openness of source code, and community (open) participation in implementation offers unprecedented opportunities for developers in DCs to develop technological capacity and collaboratively customize and implement software, these aspects could also be sources of challenges and could facilitate for routines to be extended unnecessarily in turn affecting roles and relationships. The study suggests that focusing on the notions of organizational routines helps to understand and explain organization changes and the complex interaction between the social and the technical in a specific context. Finally the study recommends points to bypass some of the challenges.