More publicly listed firms have emphasized the effectiveness of internal control in an information technology environment. Hence, this study presents a logical assessment mechanism for appraising the internal control of information technology. The strategy is based on Gowin’s Vee structure. On the theory side, this study explores the assessment items of internal controls on information environment by using grounded theory, and then confirms the items via the Delphi methodology. On the empirical side, this assessment model is verified via a multiple-case study to examine its usability in practice. This study expects that management and external IT auditors will apply such a mechanism to enhance the handling of internal control during the IT control evaluation stages.