Although the discipline of information systems (IS) development is well established, systems’ failure, abandonment, and dissatisfaction with functioning systems remain widespread. This has generated a considerable amount of literature investigating the factors seen to contribute to IS success and failure. However, little attention has been given to the possible relationships among the factors most influential in IS success and failure. Therefore, we examine the development of a successful system and compare the factors associated with the system’s success against the factors most reported in the literature as being associated with systems’ failure. Project management practices may be affected by knowing whether success and failure are two sides of one coin or different in nature. The results of our exploratory study showed that four of the six factors identified by the participants in our chosen system as being the most influential in the success of the system were directly related to the factors identified from the literature as being most associated with IS failure. Although more research needs to take place, these results would suggest a considerable relationship might exist between IS success and failure factors.