Contemporary Project and Portfolio Management Information Systems (PPMIS) have embarked from single-user, single-project management systems to web-based, collaborative, multi-project, multi-functional information systems which offer organization-wide management support. The variety of offered functionalities along with the variation among each organization needs and the plethora of PPMIS available in the market, make the selection of a proper PPMIS a difficult, multi-criteria decision problem. The problem complexity is further augmented since the multi stakeholders involved cannot often rate precisely their preferences and the performance of candidate PPMIS on them. To meet these challenges, this paper presents a PPMIS selection/evaluation approach that combines TOPSIS (Technique for Order Preference by Similarity to Ideal Solution) with intuitionistic fuzzy group decision making. The approach considers the vagueness of evaluators’ assessments when comparing PPMIS and the uncertainty of users to judge their needs.