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This study investigated the crucial factors for measuring the success of the information system used in the e-learning process, considering the transformations in the work environment. This study was motivated by the changes caused by COVID-19 witnessed after the shift to fully online learning environments supported by e-learning systems, i.e., learning emphasized with information systems. Empirical research was conducted on a sample comprising teaching staff from two European universities: the University of Novi Sad, Faculty of Technical Sciences in Serbia and the Polytechnic Institute of Castelo Branco in Portugal. By synthesizing knowledge from review of the prior literature, supported by the findings of this study, the authors propose an Extended Information System Success Measurement Model—EISSMM. EISSMM underlines the importance of workforce agility, which includes the factors of proactivity, adaptability, and resistance to change, in the information system performance measurement model. The results of our research provide more extensive evidence and findings for scholars and practitioners that could support measuring information system success primarily in e-learning and other various contextual settings, highlighting the importance of people’s responses to work environment changes. © 2023 by the authors.