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For the past several decades, user involvement has been considered as the main factor to lead to user satisfaction, which plays a vital role in system success. The objective of this paper is to explore the challenges or risk expected when involving user in development phase, to define the characteristic of user when involved in development phase, and to define the quality of user participation in order to contribute to system success. We have conducted a case study of software development project and collected qualitative data using questionnaires and open-ended interviews. The result based on the case study and qualitative data showed that several challenges of involving user in the development process. The case study data analysis also revealed that user-s feedback significantly contributes to the system success. Knowledgeable users and valid feedback are essential elements of user involvement through the software development process. The project team also need to manage the challenge or risk properly and know how to handle them in order to avoid any complication during the development process.