Abstract: Recently, assessing the effectiveness of the Web-based Management Information Systems (WBMIS) from the perception of employees such as educationalists is increasingly needed as it has important contributions to organizations. Therefore, the primary focus of this study is to develop an assessment model to evaluate the effectiveness/net benefits of WBMIS from the developmental vision of educationalists which in turn positively affect the whole education process. To do so, a preliminary study is conducted through a semi-structured interview for 20 educationalists, in which, the thematic approach is employed for analysis purposes. Second, the theoretical basis of the relationship among study factors: information quality, system quality, service quality, interaction design quality, decision support quality, user satisfaction and the net benefits of WBMIS are explored in a more rigorous and comprehensive manner. In the light of the preliminary study and critical review of Management Information System (MIS) theories, it is found that the user satisfaction has a mediating role in the relationship between equality factors and the WBMIS benefits. Accordingly, an extended assessment model is proposed in order to fill the gap in MIS literature and also, contributes to empirical studies in the fields of Information Systems (IS) development and education technology.