Information System implementation can truly be considered as a “success” when a significant number of users have used the Information System (IS) on a continued basis. The lack of continuous use of an Information System has been identified as one of the major causes for IS project failure. The reason for the lack of an IS continuous use is due to its inability to satisfy users and to avoid user dissatisfaction. While many studies have investigated user satisfaction, user dissatisfaction seems to be ignored in IS literature. The purpose of this study is to investigate the factors that influence user satisfaction and the factors that influence user dissatisfaction. A study of the literature along with a qualitative study was conducted to explore these factors. The qualitative study was conducted by interviewing staff from a tertiary institution, who continually use an Enterprise Education System to support teaching. The results suggest that it is important not only to make users satisfied but also to avoid user dissatisfaction.