The purpose of this study is to develop and validate a new expert system for detecting failure in the web system interaction design. This system aims at helping the top management and IS developers to justify IT investment through diagnosing the interaction capabilities of user interface and online communication tools. The research methodology consists of a five-step process which facilitates the development of the expert system and, consequently, the diagnosis of the interactivity features of the Web information system. The five process components are as follows: reviewing related empirical studies; extracting the core diagnosis factors; designing and implementing the expert system; testing the expert system; and deploying the expert system. The validation achieved by a sample of IS developers and professionals demonstrates the effectiveness of the proposed detection framework. Based on the feedback collected from the IS developers who tested the developed expert system, the proposed framework seems promising, and can be even be applied in other related area such as human resources management.