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Generated by internal synergy relationships in project portfolio (PP), project portfolio synergy benefits (PPSBs) are essential for enterprises to achieve their strategic objectives. However, few studies have been conducted on measuring PPSBs, which hinders managers from making rational use of PP synergy relationships to realize and improve PPSBs. This research deals with this issue by constructing a PPSB measurement model. First, the PPSB measurement model elements, including PP synergy, PPSB measurement criteria, and PPSB influencing factors, are identified. At this stage, to integrate PP synergy into the measurement model, a new method that emphasizes project similarity based on the project niche is proposed to quantify it. Then, a system dynamics model is developed by quantifying the causal relationships within these elements to measure PPSBs. Finally, the proposed model is demonstrated and validated with a numerical example. Results show that this model can help managers to measure and optimize PPSBs. To our knowledge, this proposed model is the first to realize the measurement of PPSBs, enriching the literature on project portfolio management and providing managers with a tool for enhancing the PPSBs following the organization strategy. [ABSTRACT FROM AUTHOR]