In recent years, organizations across many industry sectors, including the higher education sector (TES), have begun implementing digital technology-enabled digital transformation (DX) projects. Such transformations promise a dramatic improvement in business performance by radically changing organizational processes, services, structure, culture, and even business models. Despite promised improvement in business performance, implementing the DX project is complex. This is mainly because organizations are destined to experience challenges that impede the successful journey of digital transformation projects. As a result, many DX projects have failed to deliver much-expected benefits. Given the importance of DX in a business context, it is crucial to investigate what challenges types occur and how they affect DX project success. As DX is a new and emerging phenomenon, more scholarly literature about the impact of DX challenges currently needs to be found. Such literature is primarily descriptive and needs to be more specific in explaining how various types of DX challenges affect multiple dimensions of DX success from the project management perspective. Against this backdrop, this research project has been undertaken to examine the impact of four types of DX challenges on three specific dimensions (i.e., schedule, budget, and scope), rooted in the traditional project management literature, for measuring DX success. Addressing such an impact is essential to devise the most appropriate actions needed by organizational management to avoid the expensive failure of DX projects. A research model has thus been developed by reviewing the existing digital transformation challenge literature. The proposed model has been qualitatively evaluated positively using a single in-depth case study approach. Qualitative data collected through interviews with multiple stakeholders were analyzed using deductive coding and directed content analysis. The case study findings confirm that only userrelated challenges, as well as organizational challenges, are found to have a broader impact on DX project success as opposed to technical challenges and Legal and security challenges. The findings further confirm that out of three dimensions (i.e., schedule, budget, scope) measuring DX project success, only one (i.e., schedule) is found to have been affected by all four types of DX challenges. On the contrary, another dimension (i.e., scope) has only been affected by two specific types of DX challenges (i.e., user-related and organizational). Overall, these findings empirically support the model to an extent. The findings mentioned above are expected to assist the management of the participating higher educational institutes in developing a richer understanding of the negative impact of various types of DX challenges on DX project success. From the scope perspective, such findings emerging from this study relate to the context of the participating higher educational institute only. Although management of similar types of higher educational institutes may benefit from the experience of the participating case organization, this study does not claim to generalize such findings across the entire higher education sector in Oman. Future research is thus needed to examine how such challenges would deter the success of DX projects undertaken by many other higher educational institutions in Oman