Recent statistics have shown a high percentage of IS projects that failed to fulfill the expectations of the key stakeholders by overrunning their budget, delays in the schedule, or meeting their required specifications. This indicates the importance of understanding the difficulties that impact a project's success and cause a waste of time, money, and effort in the organization. Due to this, project management and project success/failure are interesting research areas for consideration. However, the existing studies also presented the need to conduct field research in a real-life context case study to evaluate the failure factors. Furthermore, only a limited number of studies discussed the failure of IS projects from more than one point of view. The main purpose of this study is to present a deep understanding of the critical failure factors of IS projects using the stakeholder theory, especially with regard to the public sector which has a different environment from the industrial or private sector. The critical failure factors were identified by using a systematic literature review of recent studies. These factors were analyzed, ranked, and classified into three main categories: Organizational factors, People, and Technology. In addition, the collected factors were used in a real case study to conduct semi-structured interviews and have a deeper understating of these factors from the perspective of key stakeholders. This study highlights the importance of different key stakeholders who are involved in the project and identifies the most critical failure factors based on each group of stakeholders' perspective (project managers, business users, and development team). Moreover, the study highlighted several critical failure factors that were reported continuously in the previous literature such as communication issues and change management. Besides that, this study identified three factors not mentioned before in the literature such as Guideline Availability and Requirement Analyses and shed light on their impact on projects and how they lead to stakeholders' dissatisfaction. This study provides a clear picture of the relationship between the critical failure factors and the different types of stakeholders. Thus, it contributes to the research field by identifying the CFFs. Practically, it will help the organization know how to deal with critical failure challenges, which might lead to an increased project success rate.