Cloud-based Enterprise Systems (Cloud ES) offer productivity and data access benefits to higher education institutions (HEIs). However, implementing Cloud ES in HEIs is complex due to organizational structures. A doctoral research project aims to identify challenges in Cloud ES implementation and investigate the influence of stakeholder engagement on the formation and mitigation of these challenges in HEIs. A qualitative case study approach employing semi-structured interviews with key internal and external stakeholders was employed. This research contributes to the scientific knowledge concerning the unexplored area of Cloud ES implementation in HEIs, thereby enhancing digitalization success in HEIs.