Information systems and technology (IS/IT) projects are perceived as ventures that are prone to failure. An evaluation as part of IS/IT governance and control is highly important for stakeholders, to lessen the risk and the failure of such projects. However, decision-makers often encounter difficulties when evaluating and making decisions regarding the continuation of their projects. This study examines equivocal situations and the antecedents of dilemmas in project evaluations. A theoretically grounded research model postulates the influence of Content, Context, and Process of evaluation on the prevailing equivocal situations. The model, which is tested using PLS analysis, shows the impacts of the Challenges of project management, the Lack of standards, and the Sophistication of Technology on the extent of equivocal situations. This study is based on a survey of 111 projects and offers early empirical evidence attesting to the importance of well-defined project charters and senior management control in IS/IT governance.