This study was conducted in order to identify and examine the IT/IS evaluation practices employed in Saudi private organisations, and any factors that hinder such organisations in evaluating their IT/IS systems effectively. It also seeks to explore the possible relationships between IT/IS evaluation and the IT/IS organisational management. A questionnaire was developed and validated in order to provide quantitative data relating to the motivations for conducting an IT/IS evaluation, the perceived benefits of it, the attitudes towards it, and factors influencing the process. Supplementary qualitative data was obtained using interviews and case studies. The sample organisations were drawn from the databases of the Saudi Chamber of Commerce and Industry. Questionnaires were distributed to 200 private organisations, of which 79 replied. In addition, four case studies were conducted and 24 IT/IS managers were personally interviewed. The data shows that 64.6°/ of the responding organisations conducted IT/IS evaluation to some extent. It is conducted as a management process and it is not a formal evaluation. The most common reasons for conducting IT/IS evaluation were to assess work efficiency, to assess technical performance, to assess system productivity and to assess cost/benefit. The primary benefits expected from IT/IS evaluation are an awareness of necessary future strategies for the organisation and to assist in better planning for future systems (Time & Budget). The factors that could lead to resistance when conducting IT/IS evaluation were a lack of top management support, lack of the decisionmaker's awareness about the importance of IT/IS evaluation, lack of user involvement and lack of sufficient training. In addition, the main obstacles to conducting IT/IS evaluation, reported by both organisations that evaluate their IT/IS systems and those that do not, were the lack of the decision-maker's awareness about the available IT/IS evaluation methods, lack of direction from top management, and lack of training programmes in IS development. The IT/IS organisational management was found to be a major influence on the decision to conduct IT/IS evaluation in private organisations in Saudi Arabia. The significant differences found between the organisations that conduct IT/IS evaluation and those that do not were in relation to the IT/IS organisational management variables that were selected in this study. Recommendations are made to assist Saudi private organisations when evaluating their IT/IS systems.