Project evaluations are highly crucial for organizations to manage their information systems and technology project portfolios. This study postulates equivocal situations as the source of dilemmas hindering stakeholders to achieve proper evaluation and purposeful decisions. We examine three factors that are conceived to have high association with equivocal situations when evaluating IS/IT projects, Challenges in project management, Different frames of reference and Lack of evaluation data. The developed model is tested using a survey data of IS/IT professionals through PLS. We find the three factors are significantly affecting the occurrence of equivocal situations with the highest contribution come from the Challenges in project management. Multi-group examinations reveal distinct impacts of the three factors within public versus private sector and high versus low projects in the project evaluation ladder. Post hoc interviews suggest several interesting points especially on how to cope with equivocal situations.